“Schedule coffee dates with your mentor” is one of those ubiquitous career tips that seems to make sense but can be intimidating to actually follow through with. For one reason why, imposter syndrome may tell you they’re too important and busy for you. Furthermore, questions to ask a mentor that allow for a natural, not forced, but still productive conversation can be hard to come by. And now that we’re in the midst of a pandemic, navigating soaring rates of unemployment, new (often-remote) working situations, and general uncertainty, asking for someone’s time as a favor can feel even harder.
Here’s the thing, though: Now is actually the perfect time to add those virtual coffee dates to your calendar. With so much about the future job landscape unclear right now, coming up with questions to ask a mentor who can help you make a plan is to your benefit. And since so many actions have shifted to a digital space, having a meeting is actually less imposing of ask than it used to be. Now there’s no need to spend time commuting to a cafe, restaurant, or office—or look bad for showing up late because of traffic or accidentally going to the wrong Starbucks. Rather, you’ll dial in from your own space, where you feel comfortable and in control.
But there’s still that question of how to navigate the experience so that it’s meaningful for you and your mentor. Here, career experts give their best tips on questions to ask a mentor and how to reach out in a largely remote world.
How to reach out to new and existing mentors
If you already have a mentor but haven’t connected in some time, career coach Erin Hatzikostas suggests breaking the ice with suggestions that may benefit them. “One way to reignite a dormant relationship is to look for books, articles, podcasts, or other things that you think would be valuable for your mentor,” she says. After all, it sure beats saying you were laid off and are now reaching out to anyone who could possibly hire you.
Need a script to follow? Steal this one from Hatzikostas: “Hi Ellen, I was just reading an article the other day that made me think of a conversation you and I once had. It also got me thinking about how much I’d love to catch up. Would you be free to do a virtual call in the next few weeks?”
Reaching out to someone you don’t (yet) have a relationship with works slightly differently, but can be just as simple. Suzanne O’Brien, a career and job search coach, and the creator of the online course “Career Confidence,” advises connecting via mutual contacts, experiences, or stories. “Find professionals who have navigated similar circumstances, maybe a similar career change to the one you’re trying to accomplish, and also have similar personal interests,” she says. Going to the same school, studying abroad at the same place, volunteering for the same organization, or knowing the same person are all great commonalities.
After highlighting the connection in your outreach message to your new hopeful mentor, explain why you’re reaching out—and don’t be afraid to use flattery. “Show that you’ve really dug deep into their background and work,” Hatzikostas says. “For example, tell them how a specific comment they made in a post inspired you to do something. People want to feel useful, not used. By showing them sincere admiration, they’re more likely to respond and engage.”
She also recommends including a way you can be useful to them. “All connections should have reciprocity,” she says. “You may think you don’t have anything to bring to the table, but that’s simply not the case. For example, you could volunteer your time to help them on a project or connect them to someone that would be helpful for them to know.”
And if you don’t get a reply? That’s okay. It’s impossible to know what someone may be feeling or experiencing—especially amid a pandemic. Respect their silence and send another email to someone else.
What questions to ask a mentor during your virtual coffee
Since in-person meetups are in large part on hold right now, you have two options for your virtual coffee meeting: a phone call or video call. Hatzikostas prefers a video call because it better resembles the IRL experience. “Video is nearly as effective as sitting face-to-face for coffee or a drink, but without all of the hassle,” she says. “You’ll significantly increase your level of connection using video rather than just a phone call.”
“Video is nearly as effective as sitting face-to-face for coffee or a drink, but without all of the hassle. You’ll significantly increase your level of connection using video rather than just a phone call.” —career coach Erin Hatzikostas
Once the date is set, come up with questions to ask a mentor ahead of time, so that you’re not panicking mid-call about what to say. Some ideas: What’s the one most impactful thing you did in your current role to impact culture? If you were me, what one or two things would you do to ready myself for a promotion? What one or two things are you focused on right now for your own career? What could I do to help you?
Now that you’re prepped, it’s time to start the actual conversation, and you’d do well by your mentor to kick it off by stating your intention. “Even if that intent is simply an exploration, you’ll want to set the expectation up-front so the other person isn’t left wondering about this the entire call,” Hatzikostas says.
And while you might back up your intention by asking one of your pre-written questions, do remember that the call shouldn’t feel like an interview; it’s a conversation. “It is so important to see these interactions as two-sided,” Hatzikostas says. And by bringing your commonalities into the conversation, it’ll likely feel more organic, like a social coffee, not a “networking” coffee. “Genuine engagement trumps surface conversation, so by shifting your focus toward people you can relate to—and who can relate to you—you’ll find networking far more rewarding and interesting,” O’Brien says.
How to stay in touch (remotely) with your mentor after your call
After the call, emailing your mentor (existing or new) a thank-you note is a great way to show that you’re mindful of their time, while also staying at the top of their mind. O’Brien recommends a few tips for maintaining the relationship, such as sending yourself three-month reminders to reach out. “You can also set up Google alerts for their company and name, so when good news comes out that relates to them; you can congratulate them.” she says.
Chances are, after your virtual coffee, you’ll feel a renewed sense of inspiration and motivation to follow your career goals, which may well inspire your mentor, too. After all, what’s more motivating than knowing you’re inspiring others to make good on their dreams?
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