WSJ Your Money Briefing - Want to Advance Your Career? Try Reconnecting With Your Old Boss
Episode Date: November 8, 2024Starting a conversation with an old colleague or manager could help jump start your career, but contacting someone you haven’t spoken with in years can be awkward. Wall Street Journal reporter Ray A.... Smith joins host J.R. Whalen to discuss ways to break the ice. Sign up for the WSJ's free Markets A.M. newsletter. Learn more about your ad choices. Visit megaphone.fm/adchoices
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I'm JR Whalen for The Wall Street Journal.
Are you looking at ways to advance your career?
Reconnecting with a past boss or colleague could make the difference.
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.
But how do you break the ice with someone
you haven't spoken to in years?
We'll talk to Wall Street Journal reporter Ray Smith about it after the break. has a new monthly edition hosted by Capital Group CEO Mike Gitlin. Investment professionals
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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?
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's gonna 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.
What do career experts say is the value of rekindling past business relationships?
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.
And I guess this hinges on having a good history
with that person.
Oh, absolutely.
It should be someone that there were no bridges burned.
What should someone ask themselves before making contacts?
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 leads? Are you looking for a mentor? Are you
looking to develop new skills? Now 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? 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.
How about discussing or complimenting them
on what you do know is going on in their life these days?
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.
In your story, you write that the person reaching out could offer to be of service.
What could they suggest?
A couple of things they could suggest is just news articles and just job listings that they may think could interest
that person if they know exactly what that person is looking to do next or is in the
market for or if they're just curious.
So you can share information like that.
It's one way you can be of service.
You can also just offer to introduce them to somebody maybe they've been wanting to
meet or lead them to some opportunity that maybe they've been wanting to meet or lead them to some opportunity
that maybe they've been thinking about.
So you can offer some help, but the caveat, it should be realistic help.
You don't want to promise or over promise because that's not going to be a good luck.
So full disclosure, reconnecting with an old boss that I just wanted to chat with on social
media helped me get my job at the Wall Street Journal.
If you hear back from somebody and
write back and forth, how often should you stay in touch?
It really depends on how close that contact was in the past or even now. For a former colleague
or that sort of happens to be a friend now, you may want to stay in touch once a month.
And that would be considered like a close contact.
But if it's a boss that maybe they were your boss for a year, you could do that maybe once
a quarter.
That's like a mid-level contact.
If it's someone that you joked with at the water cooler or had lunch with from time to
time, but not every day or every week, maybe twice a year. That would be like an extended contact.
And an acquaintance, that would be perhaps
like a one-time vendor or a source.
That could be annually or just around the holiday.
So it really depends on the level of contact
you had with them in your business relationship.
What if you don't get a response
from the person you're trying to reach?
I would not take it personally.
And the issue is that we are all very busy.
And sometimes people miss the email
or they meant to respond and it's in drafts.
But the other thing is move on after maybe two or three tries.
It could mean that the person just
doesn't want to talk with you, but it also just could mean they're just overwhelmed and they don't have the time and people are
really busy so you should give them some grace.
That's WSJ reporter Ray Smith and that's it for your money briefing. Tomorrow we'll have
our weekly markets wrap up, What's News in Markets? And then we'll be back on Monday.
This episode was produced by Ariana Asparu. I'm your host, JR Whelan. Jessica Fenton and Michael Laval wrote our theme music.
Our supervising producer is Melanie Roy. Aisha Al-Muslim is our development producer.
Scott Salloway and Chris Zinsley are our deputy editors.
And Falana Patterson is the Wall Street Journal's head of news audio. Thanks for listening. Zscaler extended its Zero Trust architecture with powerful AI engines trained by 500 trillion
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