Mentee and mentor are words that make me cringe. They connote an antiquated, excessively formal transactional relationship where the mentor has valuable knowledge, connections, or status, and the mentee is a sponge that merely receives. 

Large corporations commonly have formal mentorship programs. But if you work for a fast-growing startup, there will be no mentors. Whether you are an individual contributor or the CEO, it's your job to figure out what you need to learn, then find and convince people to help you.

Often you'll need to reach out to these strangers without a warm introduction from someone you know. So how do you convince a stranger to help you? The best and most meaningful mentor relationships are built on reciprocity and the belief that both parties have value and can help each other. Here is my advice for building this type of business relationship.

Create a Paper Trail on the Internet

It's critical that you have a paper trail on the Internet, so that the person you're reaching out to can quickly verify that you are a real person. You'll have an even better chance of getting a reply if the person recognizes your face or name. Create and keep up-to-date social media profiles with a professional headshot of your face. Post content from these accounts over time. Make sure your following to follower count on these platforms is close to equal, or that you have more followers, so that people don't think you are a fake account.

Before you reach out to a potential mentor with an ask, authentically interact with them on social media. Did they publish an interesting blog article or Twitter thread recently? Like their work, comment with praise, or retweet a quote and tag them. Send the author a direct message letting them know you appreciate their work or opinions and why.

Outreach: Concise, With a Clear Ask 

You've ideally interacted online with your potential mentor over a period of time, built an internet paper trail to prove you're a real person, and are ready to reach out. Formulate a concise direct message or email briefly introducing yourself, include a clear call to action or ask, and the ability to opt out. Here's an example template you could modify for your outreach:

Hi Jane,

Happy Tuesday, and hope you are having a great start to your week! I read your latest blog post on early stage fundraising and found your advice incredibly helpful--especially your thoughts on how to design a great deck. My name is Hayley [link to LinkedIn], and I'm the founder of [X Company] and recent alumni of the University of Colorado at Boulder. 

I would love to ask you a few quick questions about sharing a deck with investors. Would you be open to a brief 15-minute call anytime in the next few weeks? Happy to send over a calendar invite for whatever date and time works best for you. If now is not a good time, absolutely no worries, and please don't hesitate to reach out if I can ever be of help to you or your work. Thanks in advance for your reply, and hope to chat with you soon.

Warm regards,


After you send this message, request to connect with the person on LinkedIn and include a note briefly introducing yourself. Tell them you sent them a note and that you hope to connect with them soon. Wait a week before following up. 

Offer Value

Before you have a call or coffee with a potential mentor, think through what you could offer them that is of value. Ask yourself: Can I teach this person something new about a space they are interested in? Can I offer to share their work within the various communities or newsletter lists I'm part of? Can I offer to connect them with specific talent they are looking to hire? Can I connect them with a company they would be excited to fund?

At the end of your conversation, ask if there is any other way you can be helpful to them and thank them again for taking the time out of their busy schedule to chat with you. If your potential mentor accepts any of your offers to help, always follow through. After your conversation, quickly follow up with a summary of what you discussed, any action items you agreed to, and thank them again for their time. 

Always Conduct Double Opt-In Introductions 

It's very important etiquette to learn early in your career that you should always conduct double opt-in introductions. A double opt-in introduction means that if you want to introduce people to each other, you need to ask each person for permission beforehand.

If you blindly introduce two people you know to each other, it's extremely off-putting, and leaves the recipients feeling annoyed that you didn't consult them first. They might not respond to the thread and lose respect for you. To ensure that doesn't happen, always ask both parties for permission to be introduced.