The Forgotten Middle: Why GenX Leaders Are Your Secret Weapon for AI Transformation

By Che’ Blackmon, CEO of Che’ Blackmon Consulting

Picture this: A 52-year-old Black woman executive sits in yet another AI strategy meeting. She’s navigated from DOS commands to ChatGPT, survived Y2K, pioneered remote work before it was trendy, and built bridges between Boomers and Millennials for decades. Yet somehow, she’s invisible in the conversation about who should lead AI transformation.

This is the paradox of Generation X leadership in 2024. We’re calling them “The Forgotten Middle” – and it’s time to recognize why they might be your organization’s most valuable asset for navigating the AI revolution.

The Hidden Advantage of Being “In Between”

Generation X leaders (born 1965-1980) occupy a unique position in today’s workforce. They’re digital immigrants who became fluent natives. They remember life before the internet but adapted to build the digital economy. Most importantly, they’ve spent their entire careers translating between generations, technologies, and cultural shifts.

As I explored in “High-Value Leadership: Transforming Organizations Through Purposeful Culture,” authentic transformation requires leaders who can bridge different worlds while maintaining their core values. GenX leaders have been doing exactly this their entire careers. They’ve mastered what Dave Ulrich recently identified in his updated HR Business Partner model: the ability to deliver stakeholder value across multiple constituencies while navigating technological disruption.

For Black women GenX leaders, this bridge-building extends even further. They’ve navigated not just generational and technological divides, but also racial and gender barriers. They’ve been code-switching before we had a term for it. They’ve been managing virtual teams while managing microaggressions. They’ve been innovating while being overlooked.

The Data Tells a Different Story

Recent research from MIT Sloan reveals that GenX leaders demonstrate the highest rates of successful digital transformation initiatives – 73% compared to 61% for Millennials and 58% for Boomers. Why? They combine technological adaptability with institutional knowledge and relationship capital.

Consider these overlooked strengths:

Technical Versatility: GenX leaders have manually coded websites, troubleshot dial-up connections, and learned new platforms every few years. They don’t just use technology; they understand its evolution.

Cultural Translation: Having worked under Boomer leadership and now managing Millennial and Gen Z teams, they speak multiple organizational languages fluently.

Pragmatic Innovation: They’ve seen enough tech bubbles burst to approach AI with both enthusiasm and healthy skepticism.

Relationship Equity: With 20-30 years of professional relationships, they have the trust networks necessary to drive real change.

Case Study: The Transformation Champion You Didn’t See Coming

Let me share a story from my consulting practice. Sarah (name changed), a 49-year-old Black woman VP at a Fortune 500 financial services firm, was repeatedly passed over for the Chief Digital Officer role. The position went to a 35-year-old external hire who “understood modern technology.”

Six months later, the company was in crisis. The new CDO’s AI initiatives were technically sound but culturally tone-deaf. Employees resisted, stakeholders worried about job displacement, and the board questioned the ROI.

Sarah was quietly asked to “support” the transformation. What she actually did was remarkable:

  • Built trust bridges between anxious Boomer executives and eager Millennial innovators
  • Translated AI capabilities into business value that resonated with different stakeholder groups
  • Created inclusive adoption strategies that brought along employees often left behind in tech transformations
  • Developed guardrails that balanced innovation with risk management

Within a year, the transformation was back on track. Sarah never got the CDO title, but she exemplified what I call in “Mastering a High-Value Company Culture” the power of unofficial influence in driving real change.

The Intersection of Invisibility and Indispensability

For Black women GenX leaders, this invisibility is particularly acute. As I discussed in “Rise & Thrive: A Black Woman’s Blueprint for Leadership Excellence,” we often experience what I call the “hypervisibility/invisibility paradox” – scrutinized for our mistakes while our contributions go unrecognized.

In the AI transformation context, this manifests as:

  • Being asked to fix problems but not lead initiatives
  • Having ideas attributed to others in the room
  • Being typecast as “people managers” rather than transformation leaders
  • Watching younger or whiter colleagues get opportunities based on “potential” while our proven track records are overlooked

Yet these same experiences have built unique capabilities:

Systemic Thinking: We see patterns others miss because we’ve had to navigate complex, often hostile systems our entire careers.

Authentic Connection: We build genuine relationships because we know what it’s like to be excluded.

Risk Intelligence: We understand both the promises and perils of transformation because we’ve lived through multiple cycles of “disruption.”

Inclusive Innovation: We naturally consider diverse perspectives because we know the cost of leaving people behind.

Making the Invisible Visible: Strategic Actions for Organizations

If you’re serious about successful AI transformation, here’s how to leverage your GenX talent:

1. Conduct a Leadership Audit with Fresh Eyes

Look beyond titles and formal roles. Who actually gets things done? Who do people trust with difficult conversations? Who bridges departmental silos? You’ll often find GenX leaders, particularly women of color, in these informal influence positions.

2. Create “Transformation Translator” Roles

Formalize the bridge-building that GenX leaders already do. Give them explicit authority to connect AI initiatives with organizational culture, stakeholder concerns, and change management.

3. Establish Reverse Mentoring Programs

Pair GenX leaders with both younger tech natives and senior executives. This positions them as valuable connectors rather than “stuck in the middle.”

4. Reframe Experience as Innovation Asset

Stop treating years of experience as resistance to change. Instead, recognize pattern recognition, relationship capital, and systemic understanding as innovation accelerators.

5. Address the Representation Gap

If your AI transformation team is all Millennials or all men, you’re missing crucial perspectives. Intentionally include GenX leaders, especially women of color who bring additional insights about inclusive innovation.

The Double-Bind Advantage™

Through my consulting work, I’ve identified what I call the “Double-Bind Advantage™” – the strategic capabilities that emerge from navigating contradictory expectations. GenX leaders, particularly Black women, have developed this in spades:

  • Technical enough to understand AI but human-centered enough to address fears
  • Experienced enough to have credibility but adaptable enough to embrace change
  • Diplomatic enough to navigate politics but bold enough to challenge status quo
  • Patient enough to bring others along but urgent enough to drive results

This isn’t about making the best of a bad situation. It’s about recognizing that the skills developed through navigating these contradictions are exactly what organizations need for AI transformation.

Practical Strategies for GenX Leaders

If you’re a GenX leader feeling overlooked in the AI conversation, here’s how to position yourself strategically:

Claim Your Technical Narrative

Stop downplaying your tech experience. You’ve adapted to more technological change than any generation in history. Own it.

Document Your Translation Wins

Keep a record of when you’ve successfully bridged divides – between departments, generations, or technologies. This is your unique value proposition.

Build Strategic Alliances

Connect with younger colleagues who have tech expertise but lack organizational influence. Create mutually beneficial partnerships.

Speak the Language of Value

As Dave Ulrich emphasizes in his updated HR Business Partner model, focus on stakeholder value. Frame your contributions in terms of business outcomes, not just activities.

Invest in Visible AI Skills

Take that prompt engineering course. Get that AI certification. Not because you need to become a data scientist, but because visible credentials combat invisible bias.

The Path Forward: From Forgotten to Foundational

The most successful AI transformations won’t be led by those who only understand technology or only understand people. They’ll be led by those who understand the messy, complex, human reality of organizational change.

GenX leaders have been preparing for this moment their entire careers. They’ve navigated every major technological shift of the past 40 years. They’ve built bridges across every organizational divide. They’ve translated between worlds while maintaining their authentic selves.

For Black women GenX leaders, add to this the navigation of systemic barriers, the development of extraordinary resilience, and the cultivation of inclusive leadership practices born from exclusion. These aren’t consolation prizes for discrimination – they’re competitive advantages for organizations smart enough to recognize them.

As I’ve learned through decades of transforming organizational cultures, the most powerful changes often come from the most unexpected places. The executive who’s been quietly making things work for 20 years. The woman who’s been translating between departments since before we called it “cross-functional collaboration.” The leader who’s been building inclusive cultures while being excluded from leadership tables.

Your Next Steps

The AI transformation isn’t just about technology – it’s about people, culture, and change. GenX leaders, particularly those who’ve been traditionally overlooked, bring unique advantages to this challenge.

Discussion Questions for Your Organization:

  1. Who are the informal bridges in your organization? How can you formally recognize and leverage their influence?
  2. What assumptions about “digital natives” might be causing you to overlook experienced leaders who’ve successfully navigated multiple technology transformations?
  3. How can you create pathways for GenX leaders, especially women of color, to lead AI initiatives rather than just support them?
  4. What would change if you viewed years of experience as an innovation asset rather than resistance to change?
  5. How might your AI transformation benefit from leaders who understand both the promise and perils of technological change?

Ready to Unlock Your Organization’s Hidden Advantage?

At Che’ Blackmon Consulting, we specialize in identifying and developing overlooked talent to drive transformational change. Our fractional CHRO services and culture transformation programs help organizations recognize and leverage the full spectrum of their leadership capability.

If you’re ready to:

  • Uncover the hidden innovation potential in your GenX leadership
  • Build AI transformation strategies that actually work because they’re led by people who understand both technology and humanity
  • Create inclusive leadership pipelines that leverage all your talent
  • Transform your culture to support sustainable technological change

Let’s start a conversation.

Contact us at admin@cheblackmon.com or visit https://cheblackmon.com to learn how we can help you turn your “Forgotten Middle” into your competitive advantage.

Remember: The future of AI isn’t just about algorithms and automation. It’s about the humans who can bridge worlds, translate between constituencies, and bring everyone along on the journey. Your GenX leaders – especially those you’ve been overlooking – might just be your secret weapon.

What GenX leader has made a difference in your organization’s transformation journey? Share your stories and let’s change the narrative together.


Che’ Blackmon is CEO of Che’ Blackmon Consulting, author of three books on leadership and culture transformation, and a champion for overlooked talent in corporate spaces. With over 20 years of experience transforming organizations, she helps companies save $50K+ per retained employee while building cultures where everyone can thrive.

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