Staying Friendly: Why & How to Keep in Touch with Old Bosses

Staying Friendly: Why & How to Keep in Touch with Old Bosses

By: Daniel Steingold | September 05, 2016

After we leave a job, many of us forget to stay in touch with our old bosses.

This is clearly a mistake. Old bosses not only know your background and can put in a good word for you at a potential new job or opportunity, but they can introduce you to new opportunities that they may know of.

If nothing else, they will be able to confirm to a new employer that you worked for them for any given period of time.

This all brings up an interesting question: why don’t we do a better job at keeping in touch than we do?

It’s likely in part because it takes effort, and once a professional relationship has ended, we may not know how to approach a less formal relationship.

This post will primarily cover appropriate ways in which to stay in touch with an old boss.

Holiday Cards

By wishing an old boss a “Happy Birthday,” “Happy New Year,” etc., you are showing them regular courtesy and care.

Just think of how you feel when you receive a holiday card: warm, happy, and amused. It signals that someone took time and effort to stay in touch, even if you aren’t in constant contact.

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It is probably best to avoid sending cards with any religious affiliation or offbeat humor, as these could prompt one to feel offended.

As a bonus tip, sending a card that you personally made will be generally thought of as even more heartfelt.

Also, there is no need to include anything within the card itself.

Phone Calls

You can use phone calls to alert an old boss as to recent professional and personal accomplishments.

For example, if you got a new job, you can call up your old boss and let them know. It’s never a bad idea to thank them for anything that they might have done that got you to the point where you are.

As for a more personal milestone, you can alert an old boss as to the fact that you’re getting married or are hosting an event. If appropriate, you may even want to invite your old boss to the festivities!

Phone calls are great in that you can reach your old boss directly, and can ensure that they receive your message as long as they pick up the phone.

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With that being said, they’re not the best choice in all cases, particularly when calling during the later hours of the day.

Notes or Emails

Although notes and emails are two separate ways of staying in touch, they share many similarities.

Emails and notes should be short, relevant, and to the point, or they run the risk of not being completely read or understood.

If you want to leave the impression that you actually care, there are methods of going about this.

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First of all, do not only contact your old boss when you’re looking for a job. This can set off the impression that you’re simply seeking opportunity from them.

Also, try to engage your old boss by asking them questions about how they’re doing. This communicates that you actually care and are concerned about them personally, and makes it more likely that they’ll respond and be engaged.

Social Media

Contrary to what may have been the case years ago, it is not taboo to have old bosses— along with coworkers— added on social media.

Many worry about having an old boss added on Facebook, for example, when they’re still working at a job, but there shouldn’t be anything to hide once you’re no longer in a supervisor-employee relationship.

(In fact, even while working at a job, studies show that a third of workers find being friends on Facebook facilitates the employee to be able to perform more effectively.)

Also, regardless of whether you approve a friend request, there is a high likelihood that your social media channels will be perused not only by new employers, but old bosses. Facebook, in particular, encourages this through their “People You May Know” feature.

Fortunately, a majority of hiring companies are looking for something good on social media, although according to one study, 20 percent admit that they are just looking for a reason to scratch someone off of their candidate list.

All in all, there is no one single way to stay in touch with an old boss, but the main thing that should considered is using courtesy. No one will be motivated to reply to a diatribe about yourself, nor a desperate message simply looking for a favor in return.

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