Executive Roundtable: Resilient Change in Volatile Times

Executive Roundtable: Resilient Change in Volatile Times

What Recent Organizational Upheaval Teach Us About Building Enduring Change

Featured Speaker: Jackie Cureton, Former Chief Diversity Officer of Bit.ly

Abstract

In just 100 days, we've witnessed the systematic dismantling of 60 years of DEI progress across corporate America. Programs that seemed entrenched vanished when priorities shifted. This isn't unique to any single function; it's a pattern we see across transformation efforts when change remains surface-level rather than becoming truly systemic.

In this month’s roundtable, we host Chief Diversity Officer Jackie Cureton for a candid discussion on why some changes endure while others prove fragile when tested. Using recent organizational shifts as a real-time case study, we'll work together to:

• Map the patterns that separate surface initiatives from systemic transformation
• Extract transferable lessons from high-stakes change efforts under pressure
• Stress-test our current change efforts using frameworks that predict resilience
• Share insights from our collective experience navigating organizational volatility

Key Question: If finance departments can't be "unraveled" overnight, why could entire DEI infrastructures disappear so quickly?

Why This Matters Now

In an era when 76% of transformation initiatives fail and volatility from all sides threatens organizational priorities, leaders need frameworks that transcend trending topics. Jackie's experience offers hard-won insights into building change that endures, regardless of internal or external pressures.

Perfect for executives who:

• Lead strategic initiatives vulnerable to shifting priorities
• Want to future-proof their transformation efforts
• Seek practical frameworks for sustainable organizational change
• Value candid discussion over corporate speak

About Jackie Cureton

As the former Chief Diversity Officer at Bit.ly, Deloitte and Thomson Reuters, Jackie brings strategic depth to the challenge of building resilient change. Her career spans consulting, media, and tech, giving her unique insight into how transformation efforts succeed or fail across industries.

Jackie understands that effective change requires both high EQ for navigating emotional complexity and high IQ for connecting initiatives to business outcomes. Her front-row view of the recent DEI upheaval offers hard-won lessons for any executive driving strategic change in volatile times.

Roundtable Outline

Opening: The 100-Day Unraveling (12 minutes)

• Catalyst Constellations opener - The Real Question: Why could DEI infrastructures vanish overnight when finance departments couldn't?
• Jackie's Story: From 60 years of progress to systematic dismantling—what went wrong?  How ad-hoc initiatives masqueraded as systemic change - tee up on the big three topics

Vulnerability in Your Transformation (7 minutes)

Transition question: "Before we dive into solutions, let's get honest about our own vulnerabilities..."

• Vulnerability Assessment: Rapid diagnostic for your strategic priorities
• Individual reflection: Rate your top strategic initiative on resilience
• Partner discussion: What would happen if hostile leadership took over tomorrow?
• Share one surprising vulnerability with group

Three key areas to review

1. Integration Over Innovation

• Core Insight: Surface-level initiatives get swept away; integrated systems endure.

Discussion Question Options:

• Finance Department Test: What makes finance "untouchable" in your organization? How can we apply those same principles to our strategic initiatives?
• Process Integration Audit: Where does your change initiative actually touch existing workflows? If it disappeared tomorrow, would daily operations be disrupted?
• Metrics That Matter: Is your initiative measured using the same metrics that leadership reviews monthly? Or does it have its own separate scorecard? What would it take to tie your work directly to existing corporate KPIs or established goals?

2. The Boring Middle

Core Insight: Real change happens in the unglamorous phase after initial enthusiasm fades.

• Navigating the enthusiasm cliff: When fanfare fades and real work begins
• Building momentum through mundane but essential process changes
• Maintaining stakeholder commitment during unglamorous phases

Discussion Question Options:

• Enthusiasm Cliff Mapping: Think about a past initiative. At what point did excitement fade and what happened next? What would you do differently?
• Stakeholder Fatigue Strategy: How do you maintain executive attention when your initiative is no longer new and shiny? What's worked/failed for you?

Real-Time Exercise: Pair up and practice explaining your initiative's value without using any buzzwords or exciting language. Can you make the "boring" parts compelling?

3. Resilient Architecture

Core Insight: Antifragile initiatives get stronger under pressure rather than just surviving it.

Discussion Question Options:

• Stress Test Scenario: If your biggest skeptic became your new boss tomorrow, what three things would they attack first? How would you defend each?
• Untouchable Analysis: What's one program in your organization that no one would dare eliminate? What structural protections does it have that you could replicate?
• Pressure Point Mapping: When budget cuts come (not if), where does your initiative sit in the priority stack? What would move it higher?

Closing: The Path Forward (7 minutes)

Interactive Discussion: Each person shares ONE specific action they'll take in the next 30 days to make their initiative more resilient.

Catalyst Close:

• Resource sharing for strategic integration
• Next steps for continued peer learning
• Teaser for next roundtable theme?

• Catalyst close and tie in

Jackie Integration Points within the Discussion:

• Have Jackie react to patterns she's hearing
• Use her experience to validate/challenge group insights
• Position her as both teacher and fellow practitioner