Hiring today is a major challenge for many business owners. The difficulty lies not just in sourcing candidates, but in effectively assessing experience, eliminating bias, and making choices that genuinely drive business growth. On the latest episode of The Small Business Show, we welcome Isaiah Hankel, Founder and CEO of Overqualified. Today, he shares actionable insights to empower business owners to make smarter hiring decisions in a highly competitive talent landscape.
Drawing on work with more than 20,000 professionals, Hankel says small businesses must rethink how they define value, diversity, and long-term resilience when building teams.
Start with 3 critical hires
When building or rebuilding a team, Henkel recommends a deliberate approach centered around three types of hires.
- First, hire the person least like you.
Founders often overhire in their own image, creating blind spots. However, complementary skill sets create balance and expand a company’s capabilities.
- Second, hire someone most like you.
While it may sound contradictory, Hankel said operational continuity is critical, especially when the owner is the primary revenue driver or technical expert. Hiring someone who can replicate the founder’s core strengths protects the business if the owner is unavailable.
- Third, hire someone who has already been where you want to go.
That often means targeting experienced professionals 10 to 20 years ahead in the career stage, which many of whom are now accessible to small businesses in ways they weren’t before.
The overlooked advantage
Hankel argues that one of the most underutilized resources in today’s labor market is experienced professionals over 40, 50, and 60.
Many bring decades of experience at major corporations such as IBM, Pfizer, and Apple. In prior economic cycles, that level of corporate background often came with compensation expectations beyond the reach of small firms. Today, shifting market conditions have made that talent more accessible.
Investors, Hankel added, increasingly scrutinize the depth and diversity of leadership teams when evaluating companies. Cross-generational and cross-educational diversity can strengthen a company’s strategic outlook and credibility. Yet many of these candidates are being filtered out before a human ever reviews their resumes.
When AI works against you
Artificial intelligence (AI) has accelerated both sides of the hiring equation. Hankel notes that while employers use AI tools to screen candidates, job seekers use AI to generate resumes and tailor applications. The result is a surge in resume volume, with some companies’ reports going from dozens of applicants per role to hundreds or even thousands per day.
“We don’t talk nearly enough about the kind of institutional knowledge that you could instantly have just by hiring somebody who may be being screened out by your AI tools.”
Without dedicated HR teams, small business owners face mounting time pressure and decision fatigue. Automated screening tools promise efficiency, but Hankel cautions that many are optimized for short-term retention metrics rather than long-term impact.
Those systems may inadvertently favor less experienced candidates while filtering out seasoned professionals who bring greater strategic value.
Rethinking diversity
Hankel encourages business owners to broaden their definition of diversity. Beyond race and gender, diversity includes age, experience, and educational background. Rather than hiring for “culture fit,” he advocates hiring for “culture add,” bringing in people who broaden perspective and challenge assumptions.
Ageism remains a considerable issue in hiring, he said, with many professionals over 50 reporting bias.
For small businesses, overlooking senior talent may mean missing out on individuals who have already navigated economic downturns, supply chain disruptions, and industry shifts.
That lived experience, Hankel argues, strengthens resilience.
Nevertheless, Hankel’s upcoming book, Too Good to Get Hired, explores how modern hiring systems often overlook highly qualified professionals. Readers can pre-order or learn more about the book through Isaiah Hankel’s official website or via major book retailers.
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