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Advice / Job Search / Networking

How to (Non-Awkwardly) Reach Out to Old Contacts

According to a recent Inc. article, the most valuable people in your network are your “dormant ties,” defined as people you used to know but don’t currently keep in touch with. And while that may be true, I’d argue it’s only the first piece of the puzzle. How you reach out is just as critical as to whom.

Think about it: When an old associate contacts you out of the blue, you’re either pleased or perplexed to hear from him or her. If a former employee reaches out thoughtfully—perhaps with an article of interest, a compliment on a recent achievement, or a succinct ask—you’re much more likely to respond than if he or she feigns being your long lost best friend (it happens, and it’s not pretty).

To make sure you’re communicating the right way, here are three different methods you can use to reach out to former contacts.


1. If You Need Some Advice (From Someone Who Has Advised You Previously)

If you used to go this person for advice all the time, but you’ve simply fallen out of touch—e.g., a former boss or mentor—it’s mostly a matter of reconnecting, explaining your question, and being gracious and flexible to his or her schedule.

For example, say your first boss led the most efficient meetings you’ve ever witnessed. Now it’s your turn, and you could seriously use some pointers in crowd control. After a few sentences updating your contact and inquiring how things are, jump right in: “I remember your meetings always started on time, stuck to the agenda, and often ended a few minutes early. Now that I’m charged with managing staff meetings, I can see just what a feat that was and could really use some advice! Might I send you some questions regarding the challenges I am facing? I would really appreciate your feedback over email or a quick phone call.”

Be sure to be as specific as possible so the contact knows what he or she is agreeing to (“You were a great manager and I could use some advice,” is too open-ended). Additionally, letting your contact reach back on his or her terms (by phone or email, as works with her schedule) is more likely to get results than, “Can we meet for coffee and discuss?”


2. If You Need Some Advice (From Someone You’ve Never Asked Before)

Okay, so there is a whole cluster of people you knew well—you worked in the same office, you rubbed elbows at the same events for years—but along with looking to reconnect, you’ll be also be adding a new dimension to the relationship because you’ve never asked for a favor before.

For example, say you’re moving to a new city, and LinkedIn informs you that someone you used to see at industry functions all the time moved there a year ago. In this instance, I use the same trick as I do whenever I meet someone famous or important for the umteempth time. Instead of expecting them to remember me perfectly (overselling the connection) or saying something like “You may not remember me, but...” (underselling the connection—and not the foot you want to lead with), I reference a tangible memory of how we know each other. For example, “Hi, I’m Sara; we met at last year’s White Party fundraiser and the fashion event this May.” That makes it easy for the other person—whether he remembered you or not—to say, “Of course, great to see you again. How are you?”

Using the example above, just begin by saying, “Hi Jean, I see you’re working in Chicago now, which explains why you’re not at the marketing series I used to see you at. (Hopefully, the coffee is actually hot at the lectures you attend these days!) I’m reaching out because I’m moving to Chicago next month, and it would be amazing to get your take on the local area.”

Oversell the connection (“I have so missed seeing you!”), and you’ll sound insincere. Undersell it, and you could Jedi mind trick your contact into thinking she doesn’t know you that well (so why are you asking for help?). Finding a shared memory strikes the perfect balance,


3. If You’re Looking (Solely) to Reconnect

If you’re looking to reach out simply for the sake of not being forgotten, social media is a great option. Of course, LinkedIn comes to mind first. If you’re not already “in each other’s networks,” send a brief personal message and ask to connect. Already connected? Endorse your contact for skills you know she has.

Do you follow your contact on Twitter? Reply to a question he asks or an article he posts. (Who doesn’t love it when someone actually answers a question posed to the Twitterverse?)

As far as Facebook and Instagram, if you’re not already a friend or follower, tread carefully. If your contact uses these sites professionally, connecting, commenting, and sharing are a fine way to be in touch. However, if her account is private and features a profile photo with a family member, asking to connect over these sites will be seen as a social (and potentially out of place) move.

Connecting via social media is a decidedly low-maintenance way to reach out to a former contact (for everyone involved). It’s perfect when you want to simply say, “Hello.”



Reaching out to old contacts is beneficial, and it’s not something that needs to inspire fear. Use the tips above to reach out as thoughtfully as possible, and odds are your old contacts will be thrilled to hear from you.

Photo of phone courtesy of Shutterstock.