How do you start looking? How do you know who to ask for mentorship? What do you say in that first message to them?

In this article, I will take you through the first steps that will lead you to the mentor that’s right for you.

Build a mentor wishlist

Finding a mentor is a lot like finding a college or a company; start with a set of questions that will help you understand what your wishlist is, then separate your wishlist into ‘buckets’ based on your expectations of those potential mentors. I recommend rebuilding this list every six months or so to prompt you to reflect on your past intentions, and check in with yourself to ensure that your mentors are still fulfilling your needs. Here are some prompt questions to help you build your wishlist. Follow along in your notepad or notes app!

Who...

• Do you look up to?
• Has the title or job you want today or want to try someday?
• Is different from you in a way that you respect?
• Is an inspiration to you in a different area of the company?
• Did you pair with and learn a ton from?
• Do you have 50 questions for?
• Would you pay to be a fly on the wall for their meetings?
• Do you want a quote from in your next promotion packet?

Now that you have a list of folks, sort each person on the list into one of these three buckets:

1. Bucket one – the dream. ‘Never gonna happen.’
2. Bucket two – the stretch. ‘It’s a stretch but it’s possible.’
3. Bucket three – the anchor. ‘I can make this happen.’

With bucket one, the goal is to focus on asking without an expectation of a response and to get them familiar with your name so that, one day, at the right time and place, they might say yes. With bucket two, your goal is to get a response from a few of them, even if it’s not the right time for a full-fledged mentorship. With bucket three, your goal is to turn at least one person into a mentor. Just like with jobs, this is a numbers game. You only need one or two to say yes, and often it’s more about timing than whether or not they want to be your mentor.

Meet your future mentor

My favorite method of getting a mentor is one that I actually learned from a former mentee. In fact, it took me a whole year to figure out that I was her mentor! This doesn’t reflect positively on my awareness of relationships, but once the wheels in my head finally started turning and I had my suspicions, I texted her and asked her outright, ‘Do you think of me as a mentor?’. She responded, ‘🙄 Yes, obviously.’ She had somehow successfully tricked me into being her mentor without telling me. I had 100% respect for it and adopted her methods thereafter.

Here’s my modified version of her method: ask for a casual chat with a low-pressure goal of getting to know them. When that goes well, schedule follow-up meetings (taking the initiative to work through any conflicts they might have).

Why take the casual, stealthy route? While formal mentorship relationships are extremely valuable, folks are busy and it’s rare for them to make a lasting commitment upfront, especially before they have gotten to know you well. Many relationships start with a serendipitous conversation and, if that goes well, it leads to the next, and then the next. For folks in buckets one and two especially, it might be easier to get them as a mentor if the process starts with a simple chat.

When you send that first message asking for a chat, try to focus on what you want to talk about in the conversation so they know what to look forward to. Here are some phrases you could use:

• I got so much value when…
• I’d like to pick your brain about…
• I’m curious to learn about…

Here’s an actual screenshot of a message I sent to a ‘bucket two’ person, Naytri, a couple of months ago.

It took me all day to muster up the courage to send that message, and I got lucky, it worked! I got a response two minutes later and we went straight to scheduling (where I made the effort to book time in our calendars) and I happily woke up early in order to get on her busy schedule. My original goal was to ask for a follow-up meeting in a month and go from there. The hard part was over!

Here’s a secret. Mentors rarely notice the buildup and trepidation behind approaching a mentorship because they usually approach a mentorship considering factors like availability, time, convenience, and how your previous interactions have gone with them. That means a yes or no is not exclusively based on your request; many factors are not in your control. Once you get a few yes’s and no’s, it gets easier.

Secure your mentorship

After overcoming the challenges of finding a mentor and getting to the first meeting, the last stage is to secure your mentorship by making it regular. I like to do this by ending the first meeting with what I got out of the conversation, queueing a follow-up initiated by me, and ensuring I’m prioritizing them the way they’re prioritizing me. Here’s an example:

• End the first meeting by articulating the received value. Thank you so much for chatting with me! It’s so clear to me that you navigated your new role amidst some serious challenges by relying on your strength of building relationships. It was helpful to hear that because I’m in the middle of doing that now. I think I might try ____ and see how it goes!
• Queue a follow-up. I’d love to have another conversation in a month or two with you where I could share how ____ goes. And I’d love to ask you more about ____. Would that work with your schedule?
• Prioritize them. Actions speak louder than words here. I make sure to pin our conversations and change my notifications so I don’t miss their messages. I also try to let them know when I’ll get back to them if I can’t respond right away and pair that with a notification. If they’re making time for me, it’s important that I also make time for them.

As you can see, the minute you can articulate the value you’re receiving and they agree to a subsequent meeting, the relationship goes from 'potential mentor' to 'definite mentor'. You can choose at the end of the subsequent meeting to make it regular or keep it casual; it’s ok to have a mentorship relationship without making it formal.

For my mentorship with Naytri, my sneaky methods were thwarted by getting her permission to use her name and post the earlier screenshot for this article. I revealed my secret plan and she kindly responded with, ‘I’d love to officially accept being your mentor ;). Secret mission accomplished.’ This just goes to show you that there’s more than one way to secure a mentorship. Apparently, it’s also ok to ask your mentor indirectly, through an article, to be your mentor.

Search for your own process to get a mentor

Searching for a mentorship can be daunting if you don't know how to secure it. You can address your fear and uncertainty with a comprehensive process that includes trying for mentorships beyond what’s in front of you, using a starter script to request your first meeting, stealing some of the above suggestions on what to say to secure regular meetings, and finding ways to ensure that your mentor feels the value that you’ve received. Once you secure a few mentorships, it gets easier to understand what your process looks like and what works for you.

When you secure a mentorship, the next chapter of fun involves discovering what you want out of your mentor, how to communicate your needs, and how to build trust with them. I’ll be posting a second part to this article that lays that out, so stay tuned! Until then, best of luck searching and securing some brand new mentorship relationships!