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Looking for a mentor? Don't ask a stranger, do this instead.

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Alexandra Paquette
Ten Thousand Coffees Team -
June 22, 2020

Ten Thousand Coffees has run hundreds of career development programs. The #1 career development request is people seeking mentorship. 60% of people are seeking career mentorship and coaching. 79% believe that networking and mentoring benefits their career. As a result, we've done a ton of research on the topic. We've summarized the most important learnings for anyone seeking mentorship.

Don't ask a perfect stranger to be your mentor

Simon Sinek has a simple but compelling way to describe What Mentorship Really Means.

You wouldn't walk up to a stranger and ask them to be your friend. It's the same concept with mentorship and why you shouldn't email a complete stranger and ask them to be your mentor. Do this and they'll most likely ignore you. Why? For the same reason you wouldn't cold email a stranger and ask them to be your friend. Mentorships are a relationship, like a friendship.

The same way you wouldn't cold email a stranger to ask them to be your friend, you should never ask a stranger to be your mentor. Mentorships are a relationship, like a friendship. They gradually build over time. Both people have to invest in building the relationship. And both people have to benefit from it.

Friendships gradually build over time. They require both people to invest in the relationship, and to get value out of it. You're a stranger to them, and you're asking for something very precious - their time. But they don't know how you operate, so you have no credibility. So it's unclear how they can get value out of the relationship, or if it's a good investment of their time to help you.

Mentorship is a two-way street

"Mentor relationships aren't mentor-mentee, it's not just teacher-student, but rather it's mentor-mentor."
- Simon Sinek

Just like with any relationship, it's a two-way street. This is the trouble with most mentorship programs, they expect a perfect match and a heavy commitment right from day one. It's like going on a first date and expecting to get married. It's a big commitment before you know if you're even compatible with the other person.

A strong network > Mentorship alone

A mistake that many people make in seeking a mentor is only focusing on one person, rather than building a network of connections. In our research with enterprise employees, 77% have 2 or less people supporting their career growth. Beyond traditional mentorship, there's many types of mentoring and coaching relationships.

If there's one thing we've learned recently, it's that you never know when you'll need the support of a professional network. You also can't predict the kind of support you're going to need. Searching for a new role, stretching into a new discipline, building a new skill all require different connections and support. There's a lot of ways to learn from others that you'll miss if you focus on traditional "mentorship" alone. As a result, it's important to focus on building a strong network of people you can turn to (and who can turn to you as well!) rather than just finding a mentor.

Start by focusing on your existing network

The first place you should focus is within your existing network. If there's a handful of people you've built a relationship with, start there. Start by engaging with them on the social platforms they use for business. Retweet them. Comment on their LinkedIn posts to help increase their reach. Post your own content drawing on their insights. They'll be much more willing to help if you've invested in building the relationship.

The silver lining of the transition to remote work is that people are more people are open to virtual coffee than ever. This means you're no longer limited to people who are in close proximity to you.

People are more open to virtual coffee than ever. 23% have recently started doing virtual coffees because of social distancing.

Look within two skip levels

In our research, the most successful career conversations happen between people within two skip levels. For example, if you're an intern, look for someone at a manager level. They've recently faced some of the challenges you're facing, like managing the school to work transition. This helps them share their experience and you get tangible takeaways.

“The ideal experience gap is 5-10 years. That far out, the mentor is experienced but can still remember what it felt like to be in their mentee’s shoes."
- First Round
Illustration: Look within two skip levels
Illustration: Look within two skip levels

Set specific goals

Typically these relationships start from a moment of need - there's a specific problem that you're looking to solve. Asking for help without a clear goal in mind is a surefire way to get rejected. Successful people get a lot of these requests, so you need to do your homework first.

Start with...

  • What's a current obstacle you want to overcome?
  • What do you want to accomplish professionally in the next three months?
  • Is there a career transition you're considering?

Being specific about what you need help reduces their mental load on how they can help you. Specific challenges are much easier to help with than asking for general career advice. On the flip side, don't be overly direct. Asking for introductions or a job right off the bat is not a good look.

Don't ask for mentorship, start by asking for advice

Choice of words matters a lot. First Round shares that using the word "mentor" was the biggest reason the mentors they spoke to were dissuaded from talking to someone. Mentorship is time consuming, and with so many competing priorities a lot of people don't want to make that commitment.

Nearly all of the mentors we spoke to identified use of the word as the number one reason they were dissuaded or disinclined to talk to someone. It carries some negative connotations with it: it’s a time suck, it implies a very close relationship with someone you may barely know and it sounds like a long-term commitment. Direct asks like, “Will you mentor me?” are a universal turn off.

This is true in our research as well. When we've asked people whether they are a mentor, the answer 90% of the time is no. But when we ask if they've helped someone out with career advice, most of the time they have.

When you're trying to build a new relationship - start small. Ask for advice on a couple of specific topics. Ask open ended questions. The aversion to the word mentor particularly for people in the earlier and mid stages of their career. They don't feel like they have the authority or seniority to be a mentor. When people think of mentors, they often think of seasoned executives.

Be a desirable mentee

Before you reach out to someone else to ask for help, try to solve the problem on your own. Focus on actively building your career, and demonstrate that every day.

How to be a desirable mentee
How to be a desirable mentee
  • Be great at what you do. The best way to progress to the next level is to build a track record of success. If people see that you're focused on excelling at your current role, they'll be more motivated to help you get to the next level.
  • Be an avid learner. Follow thought leaders in the field you're interested in. There's a ton of great content you can learn from, and high quality free courses you can take.
  • Take initiative. Look for chances to increase your responsibility in your current role. If you see an opportunity to improve or innovate - take advantage of it without being asked. Finding your own ways to level up will set you apart.
  • Show that you're willing to put in the work. Development takes time and commitment on top of your daily responsibilities. Do this by always being prepared.

Write a strong, personalized outreach message

People want to feel like you've taken the time to do your research. Personalizing the outreach is key if you want someone to respond. It shows that you respect their time.

5 tips for a strong personalized outreach message
  • Focus your outreach on them, not on yourself. Give a compliment about something they've accomplished, or comment on a piece of content they've done. Tell them specifically what you liked about it. Give some value by sharing another piece of content you read recently on the same topic.
  • Establish some common ground. People are more comfortable when they see some similarities between you. This could that you went to the same school, you have common interest, or have a shared connection. Similarity helps build trust.
  • Say why you're specifically asking them to help you. Is their career path similar to what you're interested in? Are they an expert in a particular skill that you're looking to build? A good rule of thumb is if you could send the same message to another person, it's not personal enough.
  • Keep your outreach short, and focus on readability. Your message should be four short paragraphs tops. Including line breaks and white space is also easier to read. Close with a Call to Action (CTA).

End with a CTA asking if they're willing to help you

You might think the best way to close your request is to suggest some times to meet, but that could actually hurt you. Suggesting times in your own schedule is self-serving and can be very off-putting. They haven't even agreed to help you yet. Asking for a meeting triggers people to fear losing precious time. Instead, close with asking if they're interested in helping.

Gong compared three types of CTAs:

🚫 Specific CTA: Asks for a meeting using a specific day and time
Are you available to meet on Tuesday at 4pm?
🚫 Open-ended CTA: Asks for a meeting, but it’s open-ended
👉 Example: Do you have time next week to meet?
✅  Interest CTA: Asks for interest, not a meeting.
👉 Example: Are you willing to help answer a couple questions I have about product marketing?

Note: This applies for your cold outreach, but not once you've gotten a confirmation of interest, or willingness to help. Once you've confirmed interest, that's when you should close your email with a Specific CTA, asking for a meeting with a specific date and time.

Show up prepared

You asked for the meeting so you're in charge of leading it. Same as you'd prepare for a business meeting or a job interview, come prepared with an agenda. Choose a theme you want to address, and a list of questions that will help you get clarity. Keep in mind: You're asking them to share their experience, not to solve your problems.

As you're going through the questions, ask follow-ups. Focus on listening to their answers to each question, rather than drilling through an agenda. Asking, "can you tell me more about that?" or simply asking "why?" are powerful ways to learn, and will help you slow down.

Don't forget: ask how you can help them too. This goes hand in hand with #1. They'll be much more willing to continue to meet with you if they're learning too. Make time to ask what their goals are. Maybe there's a new technology they're trying to learn. Perhaps you could give feedback on a difficult situation they're managing with a direct report. Everyone is a teacher and everyone is a student.

These six simple tips are an easy way to nail the logistics of your virtual coffee chats.

6 tips for a successful virtual coffee
6 tips for a successful virtual coffee

Keep things organic and informal

Your agenda is a guide, not a rule book. If the conversation branches off into different directions, let it flow. You likely won't get the answers to every question on your mind in one meeting. Your goal is to build a relationship, and the best way to do that is that you both enjoy the chat.

If there was some natural chemistry, and the conversation flowed, you can ask if they'd be willing to chat again. Keep in mind this person likely has a lot on the go, so be reasonable with what you're asking for. Ask to follow up in a month once you've put some of their advice into practice.

Many mentorship programs set rigid rules like how often you have to meet or how you have to log your meetings. That's not fun for anyone. Things come up, other priorities get in the way. Once you've built the relationship, aim for a loose schedule. Once a month for a quarter is a lot easier to manage than every Wednesday at 9am.

Follow-up and continue to build

After the meeting, send a follow-up message thanking them for their time. The principles of writing a good thank you note are very similar to writing good outreach. Taking the time to close the loop each and every time creates a great first and last impression.

4 tips for a great thank you note
4 tips for a great thank you note
  • Thank them for their time. You'd be surprised that even many experienced leaders experience self-doubt. They want to know they were helpful.
  • Let them know what you learned. One or two key takeaways show people you were listening, and that you plan to put what you learned into action.
  • Offer something to help them. This could be an introduction you can make for them, or an interesting article related to your chat.
  • Keep your outreach short, and close with next steps. These can be your next steps, or if they offered something in the meeting, you can list that too. If you plan to continue to meet, set expectations of when you'll reach out to them next. If you only plan to meet once, your next step might be as simple as staying connected on Linkedin.

In Summary

Looking for a mentor? Don't ask a stranger, do this instead:

How to find a mentor
How to find a mentor

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