How to Email Someone You Haven’t Talked to in Forever

At some point in our careers, we find ourselves in need of help from others — whether it’s to make a direct connection to a hiring manager, to gather information on a prospective client company, or to get help in learning about a new industry quickly. However, over the years, we often lose touch with people in our network as work, family, and other demands fill our limited time. As if reaching out to ask for help wasn’t hard enough, what do you do when the person whose help you need is someone you haven’t spoken to in over a decade?

As an executive coach, I have seen clients in this situation many times. Building and nurturing our personal and professional networks is essential for career success, with research showing that robust networks lead to better opportunities, faster advancement and greater status, among other benefits. When it would help you to ask for help from someone you’ve lost touch with, you don’t need to feel awkward. Just keep a few things in mind:

Shift your perspective. The last thing any of us want is to be seen as the person who reaches out to someone only when we need something from them. No one wants to be that person. This concern, alone, can prevent us from getting back in touch. Changing the way you view your outreach to this person can make the initial contact feel a little less uncomfortable. I have often reminded clients, “Guess what? They also haven’t contacted you over the last 10-plus years. They might be really glad to hear from you.” Taking the perspective of shared responsibility for the lapse in contact, or looking at your outreach as a positive event and a good reason to re-establish a relationship with your contact can be helpful in overcoming the mental hurdle to your initial outreach.

Acknowledge the absence of contact. Calling out the elephant in the room can also ease the awkwardness. If the context of your relationship was less formal, say a college or graduate school classmate, you might use a bit of humor and say something like, “Blast from the past” in the subject line. If your relationship was more formal in nature, perhaps a former boss or client, you might say something like, “Re-connecting” in the subject line. In my own experience sending these types of email, and that of my clients, when there is name recognition by the person receiving the email, the response rate has been over 90% with one of these subject lines. Early in the body of your email, you can acknowledge it’s been a while since you’ve been in touch and briefly update them on what you’ve been doing professionally. This will also help provide useful context for your request.

Pay attention to tone. Making requests that sound either desperate or demanding can result not only in your request being denied or ignored, but it can also taint the other person’s view of you. You want your tone to appear confident in that you believe that this request is something that the other person is able to say “yes” to. At the same time, you also want to make it somewhat tentative by recognizing that they are likely very busy. You can also offer to make it easier for them by saying something like, “Please let me know how I can make it easier for you to fulfill this request.” They may ask you to draft an email that can easily be forwarded or to send additional information.

Give them an out. In recognizing that you are aware that they may be short on time to fulfill your request, giving the other person an out will also help both you and your contact to save face in the event that they cannot help you. You might say something like, “I’m sure you are very busy, so if this is not a good time for you (or if you don’t feel like you know this person well enough to make an introduction), I completely understand.”

Offer to reciprocate. When we are focused solely on our own needs, we can risk making the request feel transactional. By viewing your request in the context of a larger, reciprocal relationship and asking how you can be helpful to the other person, you help to build the relationship. By saying something like, “Please let me know how I can be helpful to you, either now or in the future,” you open the door for them to reach out for help when they need it. Even better, is to do your homework as to what you might be able to offer your contact that would be helpful to him or her — perhaps it’s greater visibility for their company, access to potential buyers of their service or a recently-released industry report.

Show appreciation. Regardless if your contact is able to help you, letting him or her know in a short note that you appreciate their reply and are glad to be back in touch can leave both parties feeling good about the interaction. If they are able to help you with your request, sending a follow-up thank you note and even a small gift like a bottle of wine or gift card for their favorite coffee shop can be a nice touch. I once reached out to a former colleague to ask for an introduction to the Head of Talent Management at a large company, where I then had the opportunity to propose a sizable engagement. My contact had a stressful job, so I gave her a gift certificate to a day spa, even before I knew the outcome of my proposal, letting her know how much I appreciated the opportunity that her introduction created, regardless of the outcome.

Stay in contact. Now that you’ve reconnected with this person after all of these years, this is your opportunity to stay in touch. This may be something small like including this person on your holiday card list or connecting on LinkedIn (or other appropriate social media), or inviting them to have coffee or lunch when you are in their neighborhood or city.

Reaching out to those that we’ve lost touch with doesn’t have to be a huge hurdle to asking for help when we need it. By keeping the above guidelines in mind, you can gracefully bridge these gaps in a relationship to re-engage your network and build mutually beneficial relationships.