Rejected Again? Why Your Job Applications Are Weak AF... and What To Do Instead

Can I be mean for a sec?

Traditional job boards are a way of the past. They’re literally where great talent goes to die and mediocrity takes over.

I’ve spent the past two years building a team from scratch. I've never—and I mean NEVER—found my best people through LinkedIn, Indeed, or any other job board. Not once! Mind you, two years later, I’m still actively recruiting, holding out for the right fit. As an employer, the best piece of advice I ever got was to hire slow and fire fast.

So whether you’re in the game of securing meaningful employment OR you’re like me, looking to build a solid team, this post is full of gems - take what resonates, leave what doesn’t.

My best hires have come from:

• Someone in my network saying "You NEED to meet this person"

• People who slid into my DMs with specific ideas for my business

• Folks I spotted doing amazing work elsewhere and poached (sorry not sorry)

• The barista who handled a chaotic morning rush with grace

See the pattern? Real-world connections. Human-to-human interactions. People showing their skills instead of just listing them on a resume. Get into the real world and talk to strangers, please!

Employment Pitches Make Me Melt

Nothing impresses me more than someone who pitches themselves for a role.

Last week, a woman emailed me outlining how she could add to the success of my business along with links to her work. It was warm, it was real, and I have an interview with her later this week.

She didn't wait for a job posting. She demonstrated value, and piqued my interest.

Note for Job Seekers: Stop applying, start auditioning! Show your work before anyone asks to see it.

The Cover Letter Is Dead (Thank God)

WHY. TF. Are we still writing cover letters?! Those formulaic "I am writing to express my interest in..." monstrosities need to die a quick death.

Instead, when pitching yourself, try a short, personality-filled email with a specific observation about the company and one concrete idea. That's it.

Short. Specific. Value-focused.

Pro Tip: Send links instead of attachments - they’re easier to reference, open on several devices, and share with others.

For The Frustrated Job Seekers

It seems like everyone is trapped in application hell, sending countless tailored resumes into the void. Creating custom cover letters that no human will ever read.*

Stop. Right. Now.

Instead, try this approach:

• Start doing the work before you get hired. Want to be a social media manager? Create sample posts for companies you love. Want to write? Start a newsletter. Want to design? Reimagine brands that need help - create your own work.

• Go where your people are. Find events, online communities, or local meetups where people in your desired industry hang out. Build genuine connections. **

• Make it easy to say yes. Don't ask for a job—ask for 15 minutes to get feedback on your portfolio. Come with specific questions. And if they don’t bite, ask if they know anyone else they can connect you with.

• Add value before asking for anything. Share an article relevant to their business. Offer a quick website audit. Show you've done your homework.

  
  

Remember that old saying "dance like no one's watching"? Please, I beg of you to dance like EVERYONE is watching!

For My Fellow Business Owners

Traditional hiring is out the door. We’ve gotta stop posting vague job descriptions and expecting perfect candidates to appear. That’s why we're drowning in mediocre applications.

• Be vocal about your company values. The more specific you are about your culture, the more you'll attract people who genuinely align. Have a checklist, don't be afraid to say no, don't settle, and stop trying to fit a square into a circle.

• Ask your network for introductions. Regularly share what kind of talent you're looking for, even when you're not actively hiring. Ask your best talent if they know anyone as well - and offer incentives.

• Create opportunities for people to show their work. Host workshops, contests, or paid trial projects.

• Look for enthusiasm over experience. I'll take someone with fire in their belly over someone with the perfect resume any day. Know the skills and attributes than can and cannot be taught.

• Sometimes, independent contractors are the best choice. When you find someone who is an expert in their field, you may have to spend more upfront money for less time, but it’s usually well worth it.

Closing Notes: Be Findable

For both sides of this equation, the key is making yourself visible where the right people can find you.

If you're job hunting, put yourself in spaces where you're surrounded by your dream employers. Start the conversations. Get on social media (yeah, I know) and build relationships before you need them.

If you're hiring, talk openly about what you're building. Share your challenges. The right people will start offering solutions before you even post a job.

Your future dream team (or dream job) is waiting on the other side of your comfort zone. Think outside of the box.

Get outside of the box!

There’s nothing in there for you anymore.

Would love to hear your most outrageous, yet useful advice in the comments

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* "Conspiracy theory Cas", here: A lot of companies will post jobs and go through the entire hiring process as a formality for HR - already knowing who they’re going to pop into the role. Another theory I heard is that these companies are simply mining our data from resumes - phone numbers, email addresses… you name it!

** Listen! I hate networking events, you DO NOT have to go to those things. Lean more into conventions, shows, meet-ups, co-working sessions and sometimes even casual hangouts with the right crew. If you're in Toronto, check out "The Stu" for their monthly work session for women, https://thestu.ca/

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