10 Job Search-Related Questions I’m Asked Most Often (Part 1 of 2)

Every day, emails stream into my inbox from readers looking for actionable answers that’ll expedite their job search. While the specifics vary, the underlying frustration is always the same: “What the f*ck am I doing wrong?” To help you evaluate and address what’s stalling your job search, I’m publicly answering the 10 questions I’m asked most often.

Regular readers of The Art of Finding Work know that I refuse to offer comforting lies, which is what most job-search advice amounts to. Navigating today’s hyper-competitive market requires understanding and embracing how employers actually hire, not how candidates wish hiring were done.

Here are the first five candid answers in this two-part series.

1. “What’s your first piece of advice for job seekers?”

Job seekers looking for a silver bullet ask me this question. What most job seekers fail to understand is that a job search isn’t a puzzle to be solved; it’s about managing human egos. Hence my core advice: look for your tribe. Look for where you’ll be celebrated, not merely tolerated, and stop relying on online applications, which is the equivalent of playing the lottery and reduces you to an interchangeable commodity with zero leverage.

Hiring isn’t an objective science, nor will it ever be evenhanded. It’s a direct reflection of human bias, no different from how we choose friends, partners, or the content on our social feeds. We naturally gravitate toward those who mirror our values, work ethic, and mindset, and no amount of laws, legislation, or corporate mission statements will change what’s baked into human DNA. When you prioritize belonging, job offers become the side effect, not the target.

Therefore, reach out and connect (gasp!) with like-minded peers, target employers where people like you, which includes your demographic, thrive, and whose leaders speak your language. Cultural alignment is what secures a job offer, proving the power of networking. Those with savvy career management skills follow a fundamental rule: go where you’re understood.

2. “What are the top reasons job seekers struggle with their job search?”

First, their resumes and LinkedIn profiles fail to demonstrate value. A candidate’s value is measured by the impact they have on an employer’s profitability. Unless job seekers explicitly show how they increased revenue, reduced costs, or mitigated risk in past roles, employers have no reason to consider their candidacy.

Second, they’re ghosts in their profession and industry. Having zero visible footprint—no articles, posts, a blog or website, commentaries, announcements of keynote speaking engagements, or professional presence—amounts to simply not existing, even after submitting an application.

Third, their digital footprint works against them. Reviewing an applicant’s online presence is an employer’s first hiring filter. Time and again, candidates aren’t selected for an interview because of controversial posts, participation in online flamewars, or an overall unprofessional social media presence.

3. “What plays the most important role in job searching?”

Employers don’t owe job seekers anything; not to make a living, acknowledgement, feedback, or even a chance. Once entitlement takes root, it ruins your tone like a toxic leak.

There’s no stronger job search mindset than an unyielding focus on boosting an employer’s bottom line. Most job seekers approach employers as if they’re asking for a favour, rather than positioning themselves as a resource that generates revenue and protects profits.

4. “What do most job seekers underestimate?”

Many job seekers mistakenly believe that their credentials, experience, and skills automatically make them employable. They overlook the fact that they’re competing with job seekers who are younger, hungrier, better educated, and willing to work longer hours for less pay. Additionally, job seekers and those currently employed are competing with AI.

Furthermore, job seekers vastly underestimate LinkedIn’s influence on their job search and career. They foolishly treat LinkedIn as a dumping ground for past job descriptions rather than an ongoing portfolio that showcases their work and value. Recruiters and hiring managers use LinkedIn not only to find candidates but also to understand their thought process, professional conduct, and the value they’ve created. A neglected LinkedIn profile costs you opportunities because it signals that you don’t care about your professional identity.

5. “Is a cover letter necessary?”

Not including a cover letter is lazy. I don’t know a hiring manager who hires “lazy.”

A well-written cover letter is an introduction to your career narrative. It highlights your qualifications, persuades the reader that you’re the ideal candidate, and helps them picture you in the role.

Cynical job seekers love to claim that cover letters are never read. ‘Never’ is a reckless word, declaring an unsubstantiated absolute. You have no idea what the mindset of the person who’ll read your application is. Even if only 20% of recruiters and hiring managers read cover letters, in today’s hyper-competitive market, why would you discard a 20% competitive advantage?

Next week, in Part 2, I answer the remaining five questions: your value proposition, the myth of ATS-friendly resumes, networking as a self-proclaimed introvert, the importance of a personal brand, and what employers increasingly seek when hiring.