Why Your Job Search Isn't Working (And What to Do Instead)
Most job searches don’t fail because you’re not trying hard enough. They don’t fail because your resume needs another round of edits. And they don’t fail because you haven’t applied to enough roles.
They fail because hiring is never just about finding the “best” person for the job.
It’s about managing risk.
I’ve spent more than 30 years in government, including nearly 20 in leadership roles. I’ve seen hiring from both sides of the table, making decisions and navigating systems that don’t always operate as they claim.
Since 2020, I’ve coached ambitious women of colour targeting leadership roles. When their job searches stall, it’s rarely about qualifications or effort.
It’s about strategy.
Once you see how risk drives hiring and where you’re valued as an asset rather than doubted, everything changes.
Here’s what I share with my clients about what rejection really means, and how to focus your energy on the rooms where winning is actually possible.
What Rejection Actually Means
This focus on risk shows up most clearly in how rejection is communicated. When you receive familiar rejection phrases, here’s what’s often happening beneath the surface:
“We went with someone else”
Doesn’t mean you weren’t qualified. It means the other candidate felt safer to the decision-makers. Maybe they came from a competitor everyone recognizes. Maybe they knew someone on the team. Maybe their background followed a familiar pattern that required less imagination to validate.“Not a fit”
Rarely means you can’t do the work. It means you don’t mirror the people who’ve historically succeeded there. Your background, career path, or communication style doesn’t match the mental template they’re using. It’s pattern-matching disguised as assessment.“Overqualified”
Isn’t actually about experience. It’s about the hiring manager’s inability to envision you in the role as defined. They may worry you’ll be bored, leave quickly, or expect more than they can offer. Their limited imagination becomes your rejection letter.
None of this reflects your actual ability to excel in the role.
The Real Problem with Job Searching
Rejection isn’t objective feedback on your worth. Often, it’s culture fit masquerading as merit evaluation. Companies claim to want the best talent, but they frequently choose the most familiar talent.
That’s why today’s job search isn’t about sending out 100 applications to feel productive. That’s just busy work.
The real strategy is about applying smarter — knowing where your background will be read as an asset and where you’re likely to thrive.
What Actually Works
These strategies help you screen for readiness, not just opportunity — they reveal whether a company sees you as an asset from the start.
1. Study promotions, not marketing materials
Don’t just read careers pages or diversity statements. Look at who actually gets promoted:
Check LinkedIn to see whose backgrounds populate the leadership team.
Notice patterns in career progression. Do people move up from diverse entry points, or only specific paths?
Compare what the company says it values with who actually advances.
If branding celebrates diversity but leadership tells a different story, believe what you see. The promotion pattern is the truth, and sometimes it reveals the company isn’t ready for someone like you yet.
2. Ask strategic questions in interviews
Instead of generic questions, get specific about success patterns:
“Can you tell me about someone who’s succeeded in this role—what was their background and what made them effective?”
“What does career progression typically look like for people in this position?”
“Who tends to thrive here, and what do they have in common?”
Listen carefully. If every success story features the same type of person, or answers feel vague, you’ve learned something crucial about fit.
3. Track alignment, not rejection counts
Pay attention to the quality of interactions:
Notice which interviews feel like genuine conversations versus performances.
Observe where you’re naturally understood versus constantly translating your experience.
Track when your questions are welcomed versus when they create tension.
If you find yourself over-explaining your value or justifying a non-traditional path, you’re probably in the wrong room. The right opportunities won’t require that much convincing.
3 Green Flags That Matter Most
So what does it look like when you've found a place where winning is actually possible? Here are the signals worth paying attention to:
1. The energy shifts from evaluation to collaboration
You can tell when an interview becomes a real conversation:
The interviewer leans in, and time runs over.
Language shifts from “if we move forward” to “when you join.”
Questions move from testing credentials to exploring challenges together.
That shift is one of the most reliable indicators they genuinely see you in the role.
2. Your differences are treated as assets
In the wrong rooms, you manage perceptions constantly. In the right rooms:
Your non-traditional background sparks genuine curiosity.
Follow-up questions show they want to understand your perspective.
They reference specific aspects of your experience as strengths.
You’re not spending energy justifying your value — because it’s already seen.
3. They name specific challenges
Organizations ready for your leadership don’t just perform enthusiasm — they acknowledge complexity:
They describe real problems they’re addressing.
They explain what they’re doing differently and why.
They want you to make an informed choice, not just accept an offer.
Honesty signals readiness to support you and your leadership.
The Shift in Mindset
Job searching isn’t a numbers game — it’s a targeting exercise.
You’re not trying to win in every room. You’re looking for rooms where your background is recognized as leadership from the start, not something that needs defending. Where interviews feel less like proving yourself and more like exploring mutual fit.
Put your energy where green flags appear: where conversations begin with understanding, differences are treated as assets, and complexity is acknowledged rather than avoided.
That’s not settling.
That’s strategy.
This is how you stop spinning your wheels and start moving toward opportunities where you won’t just get hired—you’ll have the conditions to lead and grow.
Ready to Take the Next Step?
If you’re ready to invest in your career and figure out your next move, let’s talk.
In my private and group programs for women of colour, I support you to clarify your value, strengthen your leadership presence, and position yourself for meaningful next steps—whether that’s a promotion, a strategic career pivot, or expanded influence.
If you’d like to explore whether this support is right for you, please schedule a free discovery session here to see how we can work together.
