How to Go From Cold Contact to Your Ideal Mentor In Seven Simple Steps

---

Author’s Note: After reading the previous article in my “Mentorship” series where I shared How to Find the Right Mentor For You (and When You Should Seek the Best), the most common response I received from readers, listeners, and students was:

Can you provide more detail on the process of connecting with and nurturing the relationship with a mentor?

Patience you must have, my young Padawan.

You didn’t really think I’d leave you hanging without actionable strategies to actually connect with your ideal mentor and build a long-lasting relationship with them, did you? 😉

Ask and you shall receive!

---

As a self-diagnosed “extreme introvert,” I’ve done my best to avoid as many mixers, social events, awards parties, and otherwise for the duration of my twenty-year career in Hollywood. Yet despite my intense distaste for chit-chat and random conversations, I’ve not only built a global network of hundreds of professional contacts, colleagues, and genuine friends but also several mentors who have helped me learn, grow, solve difficult problems, avoid horrible & embarrassing poor decisions, and ultimately make not one but four major (seemingly impossible) career transitions.

Whether you are an extreme introvert like me, or you’re the polar opposite and you love in-person networking and mixers (I’ll never understand you, btw), the playing field has been leveled globally where in-person networking is not an option, and reaching out and connecting with people virtually is the only game in town.

As I mentioned in my article Why Writing Cold Emails Is the Most Important ‘Soft Skill’ You Must Master (Especially If You’re An Introvert):

1. The people you most likely want to connect with are probably introverts like you
2. Effectively writing cold emails affords you the ability to craft the perfect message for the right person (at the right time)
3. Once you progress past entry level, the vast majority of job opportunities are filled via referrals, not job postings

To most introverts, the thought of sending a cold email to someone they admire for the sake of asking a question or two is downright terrifying in and of itself. What if you ask the wrong thing? Or sound dumb? Or desperate? Or needy? That alone is enough to avoid the idea of cold outreach altogether.

Now you want me to find a mentor via email???

If you’re intimidated by the idea of reaching out to and connecting with an industry “expert,” I invite you to begin with The Socially Awkward Introvert’s Guide to Networking with Industry “Experts”.

In this article I’d like to take a much deeper dive down the rabbit hole to help you better understand the seven simple (not to be confused with easy) steps that can help you turn a cold contact into a connection, then a relationship, and potentially even your ideal mentor.

Before We Begin…Are You Clear About Who to Connect With?

Before getting too excited and thinking that after reading this article you’ll be able to transform any cold connection into your mentor, you need to be very clear about who you’re reaching out to and why. Mentorship only works if the relationship is mutually beneficial for both parties.

If you aren’t a good fit for your potential mentor, they’ll be reluctant to help, much less build a long-term relationship with you.

Conversely if this potential mentor isn’t a good fit for you, then what’s the point of putting in all the work to connect with them?

If you’re not clear on what type of mentor you require for your needs, I suggest pausing this article and learning more about How to Find the Right Type of Mentor For You (and When You Should Seek the Best) where I break down how to identify who is the best fit for your needs based on where you are in your own unique journey.

Working under the assumption you’re clear on who could potentially be your ideal mentor and they’re currently a cold connection (or a mutual acquaintance at best), let’s dive into the seven steps that will take you from cold outreach to mentorship.

How to Make a Good 1st Impression with a Compelling Outreach Message

Once you’ve identified your ideal mentor and you’re ready to reach out, don’t blow it by thinking “This is my one chance!!!” Yes, the purpose of your outreach is to eventually get a mentor. But the objective of your initial message is simply to make a good enough first impression such that you Get. A. Response.

Don’t overthink it. Here’s where to focus your attention.

Step 1: Do your homework (and provide value)

“Template” is a four-letter word. For the love of God don’t craft your outreach using templates. I’d rather you effectively spend 10 hours drafting one message that will get a response as opposed to efficiently drafting twenty-five template responses that will end up in the trash.

When you reach out to someone you hope could become your mentor, you better do a ridiculous amount of homework to better understand this person. First research as much as you can find about their own journey (podcasts, articles, and panels are great for this). Then you need to watch their work. A lot of it. If it takes you less than five hours to do the research to send an outreach message that’s truly important to your goals, you’re not doing enough research.

If you want to reach out to Emmy-winning editor-turned-director Kabir Ahktar, for example, because he could potentially be the mentor that helps you make the transition from editing to directing, don’t start your message like this:

Hi Kabir! I’m a big fan of Crazy Ex-Girlfriend, great work!

Anyone with five minutes and the internet can find this credit on Kabir’s IMDb page. Instead imagine the first impression you’d make on Kabir if you began your message as such:

Hi Kabir, I’ve been a fan of your work as both an editor and director for a long time. Of course an obvious favorite is Crazy Ex-Girlfriend (especially how you did [XYZ editorial choice] in [insert episode name here]), and I’m super excited to see your directing work on the new Saved by the Bell. But I’m also impressed with how you managed an incredibly complex season of Arrested Development. After going through the whole season (twice, to be honest), I noticed specifically that you [insert editorial choice here]. Having come from the unscripted world of awards shows and ‘Behind the Music’ makes everything you’ve accomplished that much more impressive. You have now inspired me to do the same.

While it might be a bit wordier, the latter option is more meaningful to Kabir and demonstrates this is unique & personal outreach (as far from being a template as possible). This clearly took some time. And most importantly this not only makes an excellent first impression but also provides genuine value to Kabir. Receiving this message could even be the bright spot in an otherwise crappy day.

This could also be the very beginning of a beautiful friendship.

Step 2: Have clear goals before reaching out

If you’re hoping to develop a mentor-mentee relationship with someone, they aren’t going to become your mentor after one email response. But you better make it very clear what your goals are so they can immediately ascertain whether it’s worth their time to provide you valuable advice.

One of the most common complaints I hear from people who struggle with outreach is that people never respond. If you’ve found with past outreach that most people either don’t respond or aren’t interested in mentoring you, it’s not because they are “too busy,” or “too important,” or that they don’t want to help you. It’s most likely because you haven’t made it clear how they can help you.

It’s not that people don’t want to help you. It’s that you haven’t made it clear how they can help you.

In my Insider’s Guide to Writing Amazing Outreach Emails I discuss how to use the “Magic Formula” to make it clear to the recipient why you are reaching out and where you need assistance.

“The Magic Formula” consists of three parts:

1. Making it clear where you are now
2. Making it clear where you want to be next
3. Making it clear where you are stuck and could use some advice

If you want to reach out to legendary editor Walter Murch simply because “it would be so cool” and you can tell all your friends and colleagues, he’ll see right through that. If you are reaching out for the sake of reaching out, busy people don’t have time for that.

Conversely, if you can clearly and succinctly outline your journey and next steps while making it clear where Walter can answer a very specific question to help you get unstuck, that not only provides value to you but also provides value to him. People like helping others, and if it’s clear how a simple paragraph or two can improve your life, most would be happy to oblige and provide the advice you desperately seek.

Step 3: Approach this person like a journalist (not your therapist)

If you find that you often get generic, bland, or even downright bad advice, rather than always blaming the person who gave it, take a second to look at your questions. If you want better answers, you need to ask better questions.

Despite ultimately reaching out to this person to seek advice, don’t ask for advice. This person is not your therapist whose sole purpose is to help you navigate life’s challenges. That always ends up with some variation on the same theme where your question reads as follows:

Would you be willing to provide your best advice for me to [accomplish the following goal]?

First of all, any variation on this type of question is generally difficult to answer succinctly (which lowers the probability of receiving a response at all). And if you do get a response because this person does want to help you, the response will most often read something like this:

The best advice I can give you is that it’s going to be a tough road. You’ll need to pay your dues, work hard, and be patient. Put yourself out there, meet the right people, do great work, and eventually it will happen for you like it did for me. Best of luck!

Ugh. THANK YOU, CAPTAIN OBVIOUS. I know all of this already!

The problem here isn’t the answer, the problem is your question.

Think of this process like a journalist. Instead of asking for advice and hoping that in a single email response this person solves all of your problems, ask about this person’s journey. Give them an opportunity to talk about themselves and the good choices they made to achieve the success they have (that you’re hoping to achieve yourself). Science has proven that people get more pleasure out of talking about themselves than they do food or money¹! Ask them about a specific part of their lives where if you were to make the effort to extract the advice from their experiences it would help you overcome your own challenges.

Here’s an example question that will ultimately yield much better advice:

After doing some research via IMDbPro I noticed fairly early in your career you were working on low budget reality shows, and then within 1-2 years you were working on scripted dramatic content. What were the most important steps you took that led to making this transition? 

This research-based approach is a double win: They get the opportunity to talk about themselves in a flattering light, AND you get your questions answered!

How to Follow Up & Land The First Meeting

Now that you’ve sent out a compelling first outreach message that will create a positive first impression of you, the waiting begins. If you’ve sent a succinct message that demonstrates you’ve done your homework, provides a clear picture of your goals, and asks a good question that’s easy to respond to, the likelihood of getting a response is extremely high.

Conversely, if you find that you almost never get a response, it’s probably time to review The 5 Most Common Mistakes You’re Making With Your Cold Emails (and How to Fix Them).

If you feel confident your email is solid, I’ll bet dollars-to-donuts you aren’t getting a response for one simple reason: People are just busy (and they suck at organizing email).

Does that mean it’s time to give up? Never!

Here’s how to follow up properly whether or not you get a response.

Step 4A: Follow-up (if they haven’t responded yet)

If it’s been three days and you haven’t gotten a response, it’s simple – wait longer. Your message isn’t a priority right now, and if it’s buried in someone’s inbox, it’s probably not going to become unburied anytime soon. Be patient and respect this person’s time.

At a certain point though you will have to gently nudge this person and remind them you exist. To do so effectively, I recommend using what I call “The Guilt Trip” email. At the two week mark (in the same thread as your original message) send the following polite follow-up:

Hi, I’m quickly following up to ensure my previous message didn’t get lost in your inbox. No doubt you are busy. I very much appreciate your time. Thank you.

That’s it. Simple. Yet also incredibly effective.

I get multiple outreach messages every single day, and most of them fall through the cracks. The ones that get a positive response are generally the ones where I’m politely reminded that I haven’t responded yet. As soon as I receive the message above, my first thought is, “Ugh. I totally forgot to respond to this. Now I feel bad. I should probably just respond now.”

In general, I find this follow up gets a response in an hour or less. The magic is often in the follow up.

If you still haven’t received a response, I suggest following up in 2-week intervals at least two more times. At that point if you haven’t received even a simple response, the chances of this relationship leading to mentorship are slightly higher than zero.

It’s time to move on to the next outreach message.

Step 4B: Follow up (if they do respond)

This might seem like kind of a “Duh” moment, I know. Of course you’re going to follow up if you get a response!!!! Well…not so fast. Having worked with hundreds of students in my coaching & mentorship program, I’ve learned that the only fear greater than sending an outreach message that doesn’t get a response…is getting a response!

My advice is to draft your first follow up before you send your initial message. If you have a clear and succinct question, or if you use my ninja trick of “asking if you can ask” (which I outline in detail in my Insider’s Guide to Writing Amazing Outreach Emails) you can all but predict the response in advance. If you draft your follow up questions in advance, you won’t get caught unprepared when you do get a response. Forcing yourself to draft the follow up also lends you further clarity about how to craft your initial message. The best analogy would be to imagine writing the pilot for a TV series without knowing what happens in the second episode. Writing (or at least outlining) later episodes always helps to clarify where plot points need to be clarified in the pilot.

There’s nothing worse than getting an email response from someone you admire then living with the guilt of never having followed up because you weren’t ready. Get prepared in advance so you can reply within minutes of getting your first response. You won’t come off as “too eager,” you’ll come off as organized and motivated.

Remember, if you want this relationship to eventually lead towards mentorship it’s all about first impressions. Train this person from message #1 that You. Mean. Business.

Step 5: Set up the first “Meet & Greet” meeting

As you’ll note, nowhere in the first four steps did I mention reaching out with the initial request to “have lunch and pick your brain” or “jump on a quick call when you have time.” The worst mistake you can make with your first outreach, especially if you’re seeking a mentor, is asking to meet with them immediately. The reason you reach out with simple questions from a journalistic perspective is to get good stories (from which you can extract good advice) but also to gauge this person’s level of interest in helping you achieve your goals.

If you are receiving a tepid response to your questions (and they are GOOD questions) with no real enthusiasm that often end with “Best of luck!”, then what are the odds this person is willing to carve more time out of their busy life to meet with you either virtually or in person?

Use the quality of their first response to get a sense of whether or not this relationship has a future. Your first outreach email was the first date. Does it appear this person might be willing to go out again? And conversely was their response helpful enough it’s even worth following up?

If you feel it would be worth pursuing the relationship further, this is a great opportunity to do one of two things.

1. You can thank this person for their amazing advice and ask if it would be okay to follow up again soon to let them know how things are going.
2. You can thank this person for their amazing advice and offer a lunch meeting (your treat) to show your gratitude.

I realize both scenarios are potentially scary because a “no” means the relationship isn’t going anywhere. But if you’re seeking a mentor, this is the lowest barrier of entry to take things further.

If this person responded favorably to your initial messages and their answers demonstrate a genuine enthusiasm to help you, meeting isn’t a question of whether or not they’re interested, it’s a question of how simple you make it for them. Make your request simple to confirm by offering multiple time/date options. And if you simply want to meet via Zoom, offer to send them a gift card to cover the cost of lunch at their favorite local restaurant.

Bad example: As a thank you for your advice, I’d love to take you out some time. Whenever is good for you. Hope to hear from you soon!

Better example: As a thank you for your advice, the least I can do is return the favor by offering to buy you lunch in return. Are you available in the next one to two weeks either Thursday or Friday? If not, I’m happy to accommodate your schedule.

Once all the pieces come together and you’ve had your first meeting, you’ve officially graduated to Mentorship Level 1: Meet & Greet Mentorship!

How to Transition to Long-Term Mentorship

Depending on your journey and the questions you require answers to, as I explain in my article How to Find the Right Type of Mentor For You (and When You Should Seek the Best), one meeting might be enough. Go back to step #1 and rinse. Lather. Repeat.

But if you’re interested in taking mentorship to Level 2 – The ‘Sherpa’ Mentor – your work is far from complete. It’s time to pull out the chess board and start playing the long game.

Step 6: Continue to provide value and stay in touch

Now that you’ve had a few email exchanges back and forth, and now that you’ve most likely had at least one meeting (whether virtual or in person), the next step is to stay in touch periodically to remind this person you still exist. And the best way to do so is provide value to them in one of three different ways:

1. Reach out with useful resources based on this person’s challenges and needs.

How do you know what those challenges might be? By asking them during your first meet & greet! Part of the conversation is about you and your questions, but conversely if you want to play the long game, you need to ask questions that help you better understand where you can provide value to this person in return. For example, let’s say you learned this person struggles with virtual workflows because they’ve never worked from home. You could reach out a few days after the meeting to say the following:

Thanks so much once again for our meeting. I remember you saying that you’re struggling with virtual workflows. Have you checked out this cool online course called Trello For Video Post-Production? I’ve been using it on my team and it saves us hours every week. Let me know if you have more questions, happy to help you set it up.

You’ve not only provided them value but created a scenario where they might reach out to you for continued support and guidance. Just like that, the potential mentor has already become the potential mentee.

2. Keep up with their work and reach out with praise.

I feel sorry for accountants who can never show off their kick-ass tables and cash flow charts or the doctors who can’t post the number of lives they’ve saved in a week. One of the benefits of working in the entertainment industry, however, is that eventually the public gets to see our work. Therefore, when this person’s work becomes available, whether a new film, a new episode of television, or whatever, make it a point to reach out and share with them the positive impact their work had on you. The same goes for any articles or announcements about their projects, even if they aren’t directly mentioned. Make it clear you are following them (but not stalking them…stalking is bad).

PRO TIP: To make this process easier, I use the ‘Track’ feature in IMDbPro which I highlight in my article IMDbPro for Networking: The 10 Features That Will Take Your Outreach to a New Level.

3. Demonstrate you are taking their advice…and it’s working.

This is the most important component that if done correctly will lead to long-term mentorship. If someone gave you great advice, it’s not enough to thank them. If you really want them to become your mentor, don’t just take their advice, put it into action. How does your success provide them value? It makes another person feel good about the time they invested in you.

There are few things more fulfilling to me than receiving a follow up message from a student, reader, or listener who’s gotten a positive result in their lives because of advice I’ve given. Ultimately I believe our purpose here is to help others, and knowing that I successfully did so for another is incredibly rewarding.

Even more importantly, by repeatedly following up with your progress and positive results you are training this person to believe the following: If they help you, you listen, you take action, and you get results. And what is going to be the result of this lesson? Now they want to give you even more advice and more help!

On the flip side, if you find their advice isn’t getting you the desired results…that’s okay too. It’s yet another reason to reconnect and see what you can do differently. The most important thing to demonstrate is your effort and willingness to learn.

This approach might take a while, but with patience this approach will get you results and easily lead you to having your “Sherpa” mentor.

Step 7: If you want to take it to the next level, make your intentions clear

For most people, having a “Sherpa” mentor or two is most likely enough to help you achieve your goals. But if you’re like me and you set incredibly crazy, ambitious, and what some might classify as downright stupid goals, you’re going to need more than an occasional check-in and periodic advice.

As I describe in great detail in my article How to Find the Right Type of Mentor For You (and When You Should Seek the Best), what you really need at this point is your own personal version of Mr. Miyagi.

Assuming you have stayed in touch with this person on a regular basis and clearly demonstrated that you take their advice while also providing value to them in return, it’s time to make your intentions clear. Now it’s time for the official “ask of all asks.”

There is no easy way to provide a template for this (besides, you already know how I feel about templates) as it requires a tremendous amount of context based on your relationship with this person. But the “ask” would look something like this:

Would you be willing to help me [achieve this goal]?

Yup…it’s really that simple. But you’d be shocked at how many people wait for the opportunity as opposed to asking for it. You have to put yourself out there if you expect to get what you want.

And like many of the great moments in cinema history, they’re initial answer will probably be no. Because they want to know if you truly want it badly enough.

Mr. Miyagi didn’t generously offer to become Daniel’s mentor, Daniel had to ask.

Yoda didn’t magically become Luke’s mentor, Luke had to demonstrate his willingness to learn and work hard.

Neo wasn’t automatically offered the choice between the red pill and the blue pill, he had to demonstrate he was ready to see The Matrix.

This is a turning point in your relationship, so you better be ready.

This turning point for me was the end of my first 4 hour “Bloody Sunday” ninja workout at Tony Horton’s house. It was an utter disaster. I was completely out of my league. I got my ass kicked so badly I struggled to put my hands on the steering wheel and drive myself home (it didn’t help that my hands were literally bleeding…we don’t call it “Bloody Sunday” for no reason). And Tony watched every second of my failure. In fact, he mentioned a couple years later that “I didn’t think Zack was ever coming back.”

At the end of that failed workout session I approached Tony and said, “The reason I’m here is because I’ve set the goal of becoming an American Ninja Warrior. Did I earn the chance to come back every Sunday?”

His response (thinking I’d never be back, of course), was “Sure. Come back anytime.”

And I’ve showed up almost every Sunday since. With every workout our bond becomes closer and my dedication becomes clearer to him such that he’s willing to offer more advice and go deeper with the quality of that advice.

It’s not going to be easy, but dedication, perseverance, and a willingness to step far outside your comfort zone is what it’s going to take if you require your own version of a “Miyagi” mentor.

A Single Well-Written Outreach Email Can Change Your Career

No matter the level of mentorship you require, you yield tremendous power to transform your career (and your entire life) from the comfort of your pajamas and your email inbox. You simply have to be willing to put in the work, develop a clear strategy, and get comfortable playing the long game.

By following these seven simple steps:

• Do your homework (and provide value)
• Have clear goals before reaching out
• Approach this person like a journalist, not your therapist
• Follow up (whether or not they respond to your initial message)
• Set up the first “Meet & Greet” meeting
• Continue to provide value and stay in touch
• Make your intentions clear

You too can go from drafting your first cold outreach message to having a lifelong friend and mentor who can advise and guide you to whatever audacious and inspiring goal you intend to achieve next.

Ready to Take Action?

If after reading this article you have a much clearer idea about who would be the perfect mentor for you…but you’re terrified that by reaching out you will bother them, embarrass yourself, or sound needy and desperate, I can help.

ACTION STEP #1 » Check out my Insider’s Guide to Writing Amazing Outreach Emails where I provide step-by-step instructions to send cold outreach emails that will not only get responses but can lead to priceless career advice, meetings, shadowing opportunities, mentorship…or maybe even your next gig!

Not sure exactly who the perfect mentor might be for you but you’re ready to roll up your sleeves and get dirty doing some research to figure it out?

ACTION STEP #2 »  Get on the waitlist for my brand new online Masterclass: Build Your Dream Network so I can help you build an extensive database of fulfilling projects you’d kill to work on, and then organize and prioritize the people who can open the right doors to get you opportunities on similar projects.

Good luck!

Continue to Listen & Learn:

Work With Me

Why Writing Cold Emails Is the Most Important ‘Soft Skill’ You Must Master (Especially If You’re An Introvert)

The Socially Awkward Introvert’s Guide to Networking with Industry “Experts”

How to Find the Right Type of Mentor For You (and When You Should Seek the Best)

Ep127: Chasing After the Next Gig vs. Building Your Career | with Kabir Ahktar, ACE

Insider’s Guide to Writing Amazing Outreach Emails

Ep118: Legendary Editor Walter Murch On Optimizing Creativity, Productivity, and Well-Being In Hollywood For 50+ Years

The 5 Most Common Mistakes You’re Making With Your Cold Emails (and How to Fix Them)

Trello For Video Post-Production

IMDbPro for Networking: The 10 Features That Will Take Your Outreach to a New Level

Build Your Dream Network