17


When

Tuesday, June 23, 2026
10:30 AM EST | 2:30 PM GMT | 3:30 PM CET


What to expect

Managers are expected to develop people.
But most were never trained to do it.

And yet, organizations keep doubling down:
More managers.
More expectations.
More responsibility.
But no more capability.

In this session, we go beyond theory and into reality.

Using real data and experience from Cover Genius, we’ll explore the Manager Readiness Problem,  the gap between what managers are expected to do and what they’re actually able to execute.

Because here’s the uncomfortable truth:
You can have high engagement scores…
And still fail in the moments that matter most.

This is a session about:

  • What breaks in real execution
  • Why traditional approaches don’t hold
  • And what might need to fundamentally change

We’ll Cover

1. The Manager Readiness Gap

Why organizations expect managers to develop people,  without ever building the capability to do it.

And why does this gap become critical in a world of AI, scale, and execution pressure?

2. The Engagement Paradox

What happens when:

  • Employees feel their manager cares
    …but
  • Managers aren’t showing up in onboarding, feedback, and development

We’ll break down how this shows up in real data,  and why it’s more common than you think.

3. When Structure Becomes the Problem

A closer look at:

  • A 1:3.2 manager-to-employee ratio
  • 25% of the organization is in management roles

What this creates in practice:

  • Overloaded managers
  • Underutilized managers
  • And inconsistent execution across the board

4. What We Tried (and What Broke)

From Manager On-Ramp to other initiatives:

  • Where things worked
  • Where they didn’t
  • And the key realization:
    Capability doesn’t scale with title

5. The Shift: From Performance Management → Team Investment

How real usage data exposed the gap between:

  • Intent (“we care about development”)
  • Execution (what actually happens)

And what starts to change when you shift toward:

  • Proactive team investment
  • Goal clarity
  • AI-supported execution

6. The Provocation

A question we’ll open to the room:

What if the problem isn’t how we train managers… But how many managers do we have?

Fewer managers.
Better trained.
More intentional.

Would that actually work?

 

About our expert

3-Apr-23-2026-03-55-22-7866-PM

Meet Ann Watson


Chief People Officer

Ann Watson is the Chief People Officer at Cover Genius and a seasoned People & Culture leader with a track record of scaling some of the fastest-growing technology companies.

She has led organizations through hypergrowth, doubling headcount, building executive teams, and designing talent strategies that actually work in real business conditions,  not just on paper.

Across roles at companies like MasterClass, Varo Money, and Verana Health, Ann has built the infrastructure, leadership capability, and operating models needed to scale,  while keeping a sharp focus on what truly drives performance: people.

Her work sits at the intersection of growth, leadership, and execution,  making her uniquely positioned to challenge how we think about managers, capability, and what it actually takes to build teams that perform.

What our community members are saying

Frequently Asked Questions

Who should attend 'Leverage AI in Learning – Human Learning at Scale'?

This event is tailored for L&D leaders, HR professionals, and people development strategists in SaaS, IT, fintech, cybersecurity, and AI-driven organizations who want to scale learning, increase engagement, and align outcomes with business goals.

What will I gain from attending this webinar?

You’ll leave with actionable strategies, AI-driven tools, and practical frameworks for building a learning culture that supports growth, engagement, and measurable impact. You’ll also connect with peers facing similar challenges.

When and where does the event take place?

The event takes place online on July 23rd, 2025 from 9:00 PM to 9:30 PM IDT (2:00 PM to 2:30 PM EST).

Who is the guest speaker?

Nick Bilotta, Learning Experience Manager at Discord, will share expert insights on designing learning experiences that truly impact people and business. Nick brings over 15 years’ experience across technology, hospitality, and entertainment.

How do I register and is there a cost?

Registration is free. Simply sign up using the form on this page to secure your spot. You’ll receive a confirmation email with joining details.

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Real Problems. Real Solutions.
🪄 Come for the strategy. Stay for the honesty. Leave with something useful.