The Rejection-Proof Guide for “Reaching Out” About A Job

What to Say When You Haven’t Talked in Years: Job Search Edition

Your Inbox lights up with a message from... Sara Schultz. Who??? Ohhh Sara Towers. Schultz is her married name. You remember now, vaguely. High school. AP Bio maybe? Your moms were friends, sort of). You barely knew her.

And now she's chatting you up like you’re besties. Turns out, she has the perfect retinol eye cream from her side hustle with Rodan + Fields. You feel bad letting her down (you’re more of a Sephora person), but at the same time, you feel used. Why didn’t you matter to Sara until she needed something?

You shake it off, noting that you’d never do something like that. People should only ask for favors from people they actually know. Friends and contacts they have actual relationships with.

Fast forward to 2025 and your desperate job search. It's post-pandemic, post-faux recession, post-five gazillion layoffs. You’ve done it all: applied to 500 jobs on LinkedIn, only to see that every job has at least 1500 applicants (we're not exaggerating). So far, you’ve heard back from two applications, and then been ghosted. Friends aren’t hiring. Companies you know don’t have openings. Your resources are officially exhausted.

But you need a job, so you go for it. You reach out to the random recruiter you met once, eight years ago. You hit send on the awkward message, feel super weird and self-conscious, and ultimately think of well-meaning but cringey Sara Towers (now Schultz). 

We’ve all been there, and on both sides of the experience. 

Here's a better way.

A 10-Step Plan for Reaching Out About Jobs

1. Stop blind-applying on LinkedIn. 

We’ll say it again for everyone in the back: blind LinkedIn applications have a statistically dismally success rate. Is it disappointing to see them spread out like a Soho House Thanksgiving buffet, yet unavailable for partaking? Yes it is, and we validate your experience. That said, you can look but don’t touch, not if you want to use your time well.

2. Know which LinkedIn job postings are worth your time.

Most jobs are legitimate but the chances of your blind application being seen by a recruiter, out of 1500+ applications is slim to none. Many jobs aren’t real, though. Yep, ghost jobs are a thing, and from major companies, too. We recently wrote about it here

3. Use LinkedIn strategically, not endlessly.

It’s a bit like dating apps. If you want to dedicate a few hours a week to searching the latest options, set alerts for you-specific job posts, or submit yourself occasionally, go forth. Just don’t let your life become hours of endless scrolling and applying into the black hole. And, like bumble and Hinge, when you need a break from LinkedIn “dating,” take it. Your energy is finite, and confidence crucial. 

P.S. For your birds eye view, we recently shared some alternatives to LinkedIn here.

4. Accept that your next role will likely come from someone you know, even if it's a "Sara-level" connection.

You didn’t know we were going there, did you? The truth is, most jobs actually do come from people to whom you’re connected. You might feel antsy about going out to your network, or admitting you’re looking for a job. Most of us do, but it’s completely normal. But the truth is, networking isn't gross. At some point in every person’s career, they must job search, and step one in that process is embracing the need to (ugh) …network.

5. Reframe the value of connections

None of us want to be limited, and of course, we’re not (it’s a big world out there), but there’s a level of filtering that happens when you work with brands in your sphere. Not to get too personal, but sometimes, the worst job experiences come from landing a freelance job from one of those random, unlikely LinkedIn applications. When you work with people in your extended community, there’s a level of guaranteed professionalism and compatibility, from brand equity to pay, culture, and personality-fit. 

6. Reach out. It’s not just ok; it’s the way.

Accept that you need to send the LinkedIn message, email, text, or DM. Shift your strategy from applying to the random jobs, no matter how shiny and EasyApply they look, to applying for jobs where you have an in. That in? It’s through your people. So no more job search incognito. Put yourself out there, to people you know, from your ex-work husband to a friend of a friend.

7. Be authentic in your outreach.

What Sara’s strategy was lacking was authenticity. Something simple like, “Hey, I know this is super random, and I haven’t talked to you in years, but I’m selling skincare for extra money. No pressure, but if you’re interested, lmk” would have felt a lot better. Be honest that you’re looking for a job, there’s a role they’re connected to, and you’d like their help passing your info along. Don’t overhype your relationship; be nice but real. People remember their own experiences on the job hunt, or understand that, one day soon, they’ll be in your shoes. Usually, they’re excited to help out. You don’t have to have been in each other’s weddings. You just need a solid connection.

Pro tip? Ask for something specific. And start easy. Could they give you insight into the role or company's challenges? Do they know someone on the team? Should you center your application on one certain experiences? These are better questions to start with than "Can you refer me?" Tbh, they probably don't really KNOW you anymore.

8. Don’t overlook your extended network. 

LinkedIn is actually helpful here. It’s an excellent tool for seeing where you have connections. Have your friend refer you directly, not through LinkedIn. 

9. Be prepared. 

You’re asking for a favor, so you need to do it well. It might sound obvious but it's something people overlook. Have your resume and portfolio or samples polished and ready to go. Take the time to personalize your messaging. Be prompt. Send a thank you note.

10. Focus on quality over quantity.

Instead of 500 blind applications, target 5–30 high-potential opportunities. Remember the note I sent to the recruiter I barely knew? I felt odd, and I actually didn’t hear back on that one (oh well). But I did hear back from another similar message. My contact was leading HR for a major brand, and they didn’t have any openings, but he was incredibly kind, and offered to connect me to any job or team at the brand, and put in a good word. We weren’t BFFs, but we’d had a great personal relationship, and that opened doors for me. All it took was me being brave enough to send the message. 


TL;DR:

Blind-applying on LinkedIn? Your odds are, sadly, low. Most jobs come through people you know. Yes, even haven’t-talked-since-high-school level connections. The key is doing it right:

  • Spend less time applying cold, and more time reaching out to real and extended contacts and opportunities. Friends-of-friends count.
  • Finding jobs through your network actually provides some helpful filtering.
  • Get over the awkwardness of reaching out. Acknowledge that everyone does it. And learn to do it the right way.
  • Be authentic. Acknowledge the gap since you last spoke, and don’t be afraid to ask for help.
  • Have your resume/portfolio ready, and be on your game with promptness, personal messaging, thank yous, etc. Don’t reach out until you’re fully prepped.
  • Focus on quality outreach to 5–30 targeted opportunities instead of spraying out hundreds of applications.

Bottom line: Your next job is far more likely to come from your network than from the LinkedIn black hole. So get comfortable hitting “send” (the right way!) on that message.

Of course, these tips work on recruiters like us at Artisan Talent. Find meaningful and direct ways to reach out and even recruiters busy with 1000s of applications will appreciate talent. Who knows? We may be working on your next role right now!

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