Want to Advance Your Career? Try Reconnecting With Your Old Boss

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WSJ Your Money Briefing 8 min 3 speakers 2 chapters transcribed 1 month ago
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What is the main topic discussed in this episode?

Deel/Ad Reader 0:00
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J.R. Whalen 0:15
Hey, listeners, before we get into today's episode, we want to hear from you. What financial goals are you setting for yourself in 2025? Whether it's paying off debt, building an emergency fund, or saving for that dream home, share your plans with us. You could be featured in an upcoming episode of Your Money Briefing. Send us a voice note to ymb at wsj.com or 212-416-3413. And now onto the show. Here's your Money Briefing for Friday, November 8th. I'm J.R. Whelan for The Wall Street Journal.

How can reconnecting with an old boss jump-start your career?

J.R. Whalen 0:55
Are you looking at ways to advance your career? Reconnecting with a past boss or colleague could make the difference.
Ray A. Smith 1:02
Who you know still really matters in your career. And so rekindling past business relationships helps you have more contacts that can probably lead to your next career move, or at least they may know somebody who knows someone who can lead you to your next career move.
J.R. Whalen 1:19
But how do you break the ice with someone you haven't spoken to in years?
Deel/Ad Reader 1:23
We'll talk to Wall Street Journal reporter Ray Smith about it after the break.
J.R. Whalen 1:59
Jumpstarting your career can begin with connecting with an old colleague or boss. But what should you say? Wall Street Journal reporter Ray Smith joins me. Ray, why does the idea of reaching out to a past colleague or boss make some people feel uncomfortable?
Ray A. Smith 2:14
It's really awkward. You just haven't talked to that person in a long time. And you just don't know how the person is going to respond. And you're trying to just remember sort of where you left things. And hopefully the person will respond. So it's just very uncomfortable and awkward.
J.R. Whalen 2:31
What do career experts say is the value of rekindling past business relationships?
Ray A. Smith 2:36
who you know still really matters in your career. And so rekindling past business relationships helps you have more contacts that can probably lead to your next career move, or at least they may know somebody who knows someone who can lead you to your next career move. It's all about who you know, and that's one of the reasons why it's important, especially if you already have somebody that you have a history with to rekindle past business relationships.
J.R. Whalen 3:03
And I guess this hinges on having a good history with that person.
Ray A. Smith 3:07
Oh, absolutely. It should be someone that there were no bridges burned.
J.R. Whalen 3:12
What should someone ask themselves before making contact?
Ray A. Smith 3:16
There's a couple of whys that people should ask themselves. And we talked to a number of career experts who basically told us some key questions that you should ask. One is like, what are you seeking? Is it a new job in your field? Or are you looking to meet somebody who works at a company that you'd like to work for? So you want to be connected to someone and maybe this long lost acquaintance knows that person. So you have to ask yourself several questions about the why. Are you looking for leads? Are you looking for a mentor? Are you looking to develop new skills?
J.R. Whalen 3:48
And you can look up somebody on social media, but you might not know all the details of what the person is up to these days. How do you break the ice?
Ray A. Smith 3:57
Acknowledging that it's been a minute since you all have spoken, you don't have to outright say, I don't know what you're up to or anything like that, but you can say something like, I'd love to hear how things have been going with you. You can sort of get them to tell you by asking some questions like, I'd love to hear more about what's going on with you or what's new in your job or your role or your professional development. So there are ways to sort of get at it without signaling that you really have no clue.
J.R. Whalen 4:27
How about discussing or complimenting them on what you do know is going on in their life these days?
Ray A. Smith 4:32
That's an excellent way to show, A, that you've done some measure of homework, but B, it also just says that this is not a one-sided conversation, that you are actually interested in them and in sharing rather than, I just need you right now to help me do this thing or meet this person or get this job.

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