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Chicago Leadership EXchange - The AI Skills Shift: From AI Ambition to Workforce Infrastructure

August 6, 2026 5:30 PM
August 6, 2026 8:30 PM
August 6, 2026
-
8:30 pm
ET
Chicago Leadership EXchange - The AI Skills Shift: From AI Ambition to Workforce Infrastructure
Leadership Exchange - Chicago, IL 60654

Chicago Leadership EXchange - The AI Skills Shift: From AI Ambition to Workforce Infrastructure

August 6, 2026
Osteria Via Stato
5:30 pm - 8:30 pm
Exchange details

AI proficiency is no longer a differentiator. It is quickly becoming the job description.

Within the next 24 months, 75% of AI decision-makers expect moderate AI proficiency to become standard in most non-technical roles. Not just for engineers. For everyone.

But here's the strategic tension: AI capability is already gatekeeping careers. 67% of organizations link AI skills to promotion decisions, and 50% tie them to performance ratings. Yet almost no one has defined what “good” actually looks like.

HiBob's new Insights Lab report, The AI Skills Shift: Insights from 1,200 Leaders, surveyed 1,200 AI decision-makers across six global markets and surfaced a critical reality:

  • 73% invest in AI upskilling, yet no single training topic exceeds 27% adoption. High investment, no consensus on what works.
  • Managers are the #1 group expected to build AI capability, yet only 36% are seen as highly prepared to upskill their teams.
  • The scarcest skills are not technical tricks. They are judgment. AI safety, ethics, and governance and output evaluation are the hardest skills to recruit, and they already command a 10%+ pay premium.

That gap between expectation and execution has a name: improvisation.

And it is not just inefficient. When AI skills influence promotions, ratings, and pay without shared standards, improvisation becomes a fairness problem, a consistency problem, and a credibility problem for the People function.

This Chicago Leadership EXchange is designed to close that gap.

Together, we'll dig into how to:

  • Translate vague “AI literacy” into observable behaviors you can hire for, assess, coach, and reward
  • Equip managers to evaluate and develop AI capability without making up their own rules
  • Answer the “who owns it” question inside your own operating model

Because when organizations move from improvisation to infrastructure, powerful things happen. 

This will not be theoretical. It will be candid. Tactical. Peer-to-peer.

Let's Build What's Next, Together

The next era of your organization will not be decided by which AI tools you buy. It will be decided by how deliberately you build the people systems that make AI work. The question has shifted from “How fast can we adopt AI?” to “Do our people have the skills, standards, and support to use it well?”

What to expect

This is a practitioner-only Leadership EXchange designed exclusively for internal HR & People leaders who are in the arena every day.

In one focused, high-impact evening, you'll sit shoulder-to-shoulder with local peers navigating the same AI mandates, board expectations, skills gaps, and culture realities that you are. Through facilitated, structured conversations, we'll move quickly past surface-level networking and into real dialogue, real tension, and real breakthroughs.

You can expect:

  • Curated seating aligned to your role and organization
  • Guided discussion prompts drawn directly from brand-new research on 1,200 AI decision-makers, built to unlock honest, executive-level conversation
  • Tactical insights pulled from the field, not theory: what your peers have tried, what's working, and what they'd do differently

And yes, we'll do all of this over a complimentary dinner and drinks at Osteria Via Stato, one of Chicago's most celebrated Italian tables.

As we enjoy great food and hospitality, generously supported by HiBob, we'll lean into the conversations that actually matter. The ones that sharpen your thinking, expand your perspective, and send you back to your organization stronger, clearer, and more strategically armed than when you arrived.

This is peer-to-peer leadership at its best.

Additional Benefits

  • SHRM & HRCI Recertification Credits: Earn credits while engaging in executive-level, operator-focused discussion on the most consequential talent question of the decade.
  • Complimentary Transportation: Attend with ease. Uber voucher plus comped valet, right in the heart of River North.
  • Team Advantage: We typically hold 2-3 seats per company, so bring the colleague who co-owns your AI agenda and turn the evening's ideas into momentum together.
  • Gifts & Raffle: Every attendee leaves with a special gift, plus a chance to win Amazon gift cards.
  • Exclusive Leadership Network Access: Join our invitation-only executive community with resources, virtual peer exchanges, and ongoing leadership development, guaranteeing you a seat at future dinners, EXchanges, and in-person programming.
In Partnership With
Event Snapshot
August 6, 2026
5:30 pm - 8:30 pm
Osteria Via Stato
620 N State St
Chicago, IL 60654
Invite-only · 30 seats
Practitioner-only. No vendors.
Who should attend

This complimentary Leadership EXchange is curated for senior, internal leaders in HR, People, and Talent who are navigating the AI skills shift: CHROs, CPOs, and the executives who own talent, performance, and capability building. No vendors. No consultants. Just operators in the work. Space is limited, and all registrations are reviewed by the achieve Engagement team before confirmation is sent.

what to expect

Not a panel. Not a presentation.
A practitioner-only EXchange.

Shoulder-to-shoulder with local peers navigating the same executive pressures, financial scrutiny, growth mandates, and culture realities you are.
01
Curated seating aligned to your role, organization stage, and strategic priorities
02
Guided discussion prompts that unlock honest, executive-level conversation
03
Tactical insights pulled directly from the field, not theory
04
Complimentary dinner and drinks, hosted alongside our partners
Real rooms. Real conversations.
From past Leadership EXchanges
from the room

What past attendees are saying.

Senior HR & People leaders on what made the EXchange worth their evening.
Community
The sessions are immediately applicable to real work. I was coaching a new leader on exactly the topic we covered that same week. Leaders are just like everyone else. Their jobs are just different, and this community helps you see that clearly.
MD
Madeline Des Jardins
HR Leader
Community
After 20 years in leadership, I've found a community that helps me continue to lead organizational leaders and make appropriate strategic decisions. The depth of experience in the room is powerful.
EM
Eugenia McDaniel
HR Business Partner
Executive
I am so grateful for these conversations. It is absurd to expect leaders to magically just be OK when the rest of the world is not. This community gets that.
IC
Izane Cloete-Hamilton
Business Co-Owner
Community
Thank you so much to this community and the amazing audience for sharing so many insights. The peer-to-peer learning is unmatched.
DN
Dheshnee Naidoo
HR Leader
Community
I feel so energized. This community is amazing. Thank you for the authenticity and the space to learn alongside leaders who are doing the real work.
KC
Kasee Castro
HR Leader
Executive
If all your culture does is fight fires, when there are no real fires, you've bred arsonists. This is the kind of peer dialogue you get here. Sharp, honest, and immediately useful.
CM
Christopher McCormick
Founder & CEO
Community
Terrific work and conversation. There is so much we can do with a little knowledge, ingenuity, and heart. This community fills in blanks and corrects some of the ways we go off the rails.
JH
John Howard
HR Leader
Community
I always considered myself a servant leader, until I saw that I was serving everyone else ahead of myself. Valuable conversations like this are why I keep coming back.
JG
Jennifer Gabbard
HR Leader
Community
Vulnerability normalizes mental health, which is huge in organizations. We work in hierarchical structures, so employees always look above to determine what's appropriate. Be comfortable having uncomfortable conversations. If you can't do that, you can't be an effective leader.
JW
Jeff Waldman
HR Leader
Client
achieve Engagement brought clarity, action, and responsibility to a critical part of our organization's growth. They gave our team both the space and the structure to make meaningful progress on our mission, culture, and values.
DJ
Doria Johnson
Executive Director
Urban Tilth
Member
Through this partnership, I gained invaluable tools, resources, and confidence to align my team's vision with actionable goals and navigate change with strength and focus. I highly recommend achieve Engagement to anyone committed to personal growth and driving lasting organizational impact.
AC
Alexis Crean
Director, Office of Professional Well-Being & Engagement
UConn Health
Executive
Attending sessions at achieve Engagement has been transformative. Any organization would benefit immensely from this community's guidance on creating a vibrant and inclusive culture.
RK
Ralph Kellogg
Vice President People & Training
Lutheran Family Services of Nebraska
Member
The achieve Engagement community has a way of distilling complex, often overwhelming concepts into actionable insights. It brings tremendous value to HR leaders at all stages in their talent journey. I'd recommend it to any organization looking to level-up their engagement and culture practices.
JB
Jennifer Bauer
Director, Human Capital
rf IDEAS
Partner
I've been so impressed by the achieve Engagement network. The discussions are both engaging and insightful, centered on the evolving best practices in employee experience and culture strategy. Looking forward to many more collaborations in the future.
AR
Annie Rosencrans
People & Culture Director, Americas
HiBob
Executive
achieve Engagement sessions are packed with innovative strategies and insights that are crucial for any leader looking to stay ahead in today's fast-evolving work environment. Highly recommend for any event focused on building future-ready workplaces.
SH
Sherry Harding
Chief Operations Officer
Community Bridges
Executive
The achieve Engagement community has a unique ability to take a group of HR leaders into deep and meaningful discussion. All present walk away with a new idea, share an idea, and participate at a high level within a limited timeframe.
AH
Andrea Herron
Vice President Human Resources
WebMD
Executive
achieve Engagement excels at guiding leaders to foster thriving workplace environments, driving both engagement and performance. Any organization would gain substantial benefits from this community's guidance in building a vibrant, inclusive, and high-performing culture.
JC
Jamy Conrad
VP of People & HR
TrustRadius
Member
Being part of the achieve Engagement community continues to provide the most valuable return on my investment of time. I am continually impressed by the caliber of EX leaders and the intentional objectives set forth in each experience.
DC
Darla Caughey
Director of Employee Experience
Austin Independent School District
Executive
achieve Engagement brings leadership and community together in meaningful, practical ways. It's not just talk about best practices. It actively connects people, ideas, and strategies to drive real, sustainable high performance within organizations.
JF
Jyl Feliciano
Global Vice President, People, Culture & Belonging
Highspot
Industry Leader
The achieve Engagement Leadership Network has become one of my favorite professional spaces. It's rare to find a community where you can connect with others who are truly in the trenches doing similar work. Speakers consistently share best practices they've actually tested, and I frequently walk away thinking, 'I can adapt this for us.'
BM
Bridgette McCullough
Principal Culture Advisor
Great Place to Work
Community
The sessions are immediately applicable to real work. I was coaching a new leader on exactly the topic we covered that same week. Leaders are just like everyone else. Their jobs are just different, and this community helps you see that clearly.
MD
Madeline Des Jardins
HR Leader
Community
After 20 years in leadership, I've found a community that helps me continue to lead organizational leaders and make appropriate strategic decisions. The depth of experience in the room is powerful.
EM
Eugenia McDaniel
HR Business Partner
Executive
I am so grateful for these conversations. It is absurd to expect leaders to magically just be OK when the rest of the world is not. This community gets that.
IC
Izane Cloete-Hamilton
Business Co-Owner
Community
Thank you so much to this community and the amazing audience for sharing so many insights. The peer-to-peer learning is unmatched.
DN
Dheshnee Naidoo
HR Leader
Community
I feel so energized. This community is amazing. Thank you for the authenticity and the space to learn alongside leaders who are doing the real work.
KC
Kasee Castro
HR Leader
Executive
If all your culture does is fight fires, when there are no real fires, you've bred arsonists. This is the kind of peer dialogue you get here. Sharp, honest, and immediately useful.
CM
Christopher McCormick
Founder & CEO
Community
Terrific work and conversation. There is so much we can do with a little knowledge, ingenuity, and heart. This community fills in blanks and corrects some of the ways we go off the rails.
JH
John Howard
HR Leader
Community
I always considered myself a servant leader, until I saw that I was serving everyone else ahead of myself. Valuable conversations like this are why I keep coming back.
JG
Jennifer Gabbard
HR Leader
Community
Vulnerability normalizes mental health, which is huge in organizations. We work in hierarchical structures, so employees always look above to determine what's appropriate. Be comfortable having uncomfortable conversations. If you can't do that, you can't be an effective leader.
JW
Jeff Waldman
HR Leader
Client
achieve Engagement brought clarity, action, and responsibility to a critical part of our organization's growth. They gave our team both the space and the structure to make meaningful progress on our mission, culture, and values.
DJ
Doria Johnson
Executive Director
Urban Tilth
Member
Through this partnership, I gained invaluable tools, resources, and confidence to align my team's vision with actionable goals and navigate change with strength and focus. I highly recommend achieve Engagement to anyone committed to personal growth and driving lasting organizational impact.
AC
Alexis Crean
Director, Office of Professional Well-Being & Engagement
UConn Health
Executive
Attending sessions at achieve Engagement has been transformative. Any organization would benefit immensely from this community's guidance on creating a vibrant and inclusive culture.
RK
Ralph Kellogg
Vice President People & Training
Lutheran Family Services of Nebraska
Member
The achieve Engagement community has a way of distilling complex, often overwhelming concepts into actionable insights. It brings tremendous value to HR leaders at all stages in their talent journey. I'd recommend it to any organization looking to level-up their engagement and culture practices.
JB
Jennifer Bauer
Director, Human Capital
rf IDEAS
Partner
I've been so impressed by the achieve Engagement network. The discussions are both engaging and insightful, centered on the evolving best practices in employee experience and culture strategy. Looking forward to many more collaborations in the future.
AR
Annie Rosencrans
People & Culture Director, Americas
HiBob
Executive
achieve Engagement sessions are packed with innovative strategies and insights that are crucial for any leader looking to stay ahead in today's fast-evolving work environment. Highly recommend for any event focused on building future-ready workplaces.
SH
Sherry Harding
Chief Operations Officer
Community Bridges
Executive
The achieve Engagement community has a unique ability to take a group of HR leaders into deep and meaningful discussion. All present walk away with a new idea, share an idea, and participate at a high level within a limited timeframe.
AH
Andrea Herron
Vice President Human Resources
WebMD
Executive
achieve Engagement excels at guiding leaders to foster thriving workplace environments, driving both engagement and performance. Any organization would gain substantial benefits from this community's guidance in building a vibrant, inclusive, and high-performing culture.
JC
Jamy Conrad
VP of People & HR
TrustRadius
Member
Being part of the achieve Engagement community continues to provide the most valuable return on my investment of time. I am continually impressed by the caliber of EX leaders and the intentional objectives set forth in each experience.
DC
Darla Caughey
Director of Employee Experience
Austin Independent School District
Executive
achieve Engagement brings leadership and community together in meaningful, practical ways. It's not just talk about best practices. It actively connects people, ideas, and strategies to drive real, sustainable high performance within organizations.
JF
Jyl Feliciano
Global Vice President, People, Culture & Belonging
Highspot
Industry Leader
The achieve Engagement Leadership Network has become one of my favorite professional spaces. It's rare to find a community where you can connect with others who are truly in the trenches doing similar work. Speakers consistently share best practices they've actually tested, and I frequently walk away thinking, 'I can adapt this for us.'
BM
Bridgette McCullough
Principal Culture Advisor
Great Place to Work
Agenda

An evening designed for breakthroughs.

5:30pm

Check-in & Cocktail Networking Reception

Arrive early, grab a drink on us, and step into a room full of peers who understand both the pressure and the possibility of the AI mandate. This isn't surface-level networking. It's intentional connection before we dive into the peer exchanges. Loosen up, exchange context, and start the conversations that will carry through the evening.

6:30pm

Table Seating & Strategic Peer Introductions

You’ll be seated with a curated group of leaders aligned by role and organization stage, then kick off introductions by sharing where your company sits on the AI maturity curve. These are not random tables. This is thoughtful matching designed to maximize relevance, candor, and depth. Expect quick introductions that move past titles and into what you're actually building, testing, and wrestling with.

6:45pm

Host Kickoff & Welcoming Remarks

We'll set the tone and reframe the question guiding the evening. Not “How fast can we adopt AI?” but “Do our people have the skills, standards, and support to use it well?” This moment aligns the room around shared ambition, shared pressure, and a shared opportunity: to move from improvisation to infrastructure.

6:55pm

Peer EXchange #1 - The New Baseline: Defining AI Capability for Hiring, Performance & Growth.

AI proficiency is expected to become standard in most non-technical roles within 24 months, and it's already wired into promotions (67%) and performance ratings (50%). But “AI literacy” is easy to say and nearly impossible to assess. Once rewards are on the line, vague standards stop being a training gap and become a fairness and consistency problem. The organizations that win will be the ones who can name the observable behaviors that matter, like proactively reviewing AI output and handling sensitive data with judgment, and evaluate them the same way every time.

Table Prompts: 

  • Where are AI expectations already shaping talent decisions in your organization, formally or informally?
  • Which signals do you actually trust when assessing someone's AI skill today, and which are just noise?
  • What would a shared, observable standard change about how you hire, review, and grow people?
7:20pm

Peer EXchange #2 - The Manager Readiness Bottleneck.

Managers are the #1 group organizations expect to build AI capability across their teams, yet only 36% are seen as highly prepared to do it. When systems are weak, people improvise. Managers fill the gaps with informal judgment, standards fragment, and talent decisions turn inconsistent. This isn't about individual managers falling short. It's about asking people to coach and assess a skill no one gave them the definitions, rubrics, or training to evaluate

Table Prompts: 

  • What do your managers need most right now: shared definitions, behavior rubrics, role-relevant examples, or coaching guidance?
  • Where is manager improvisation already producing inconsistent ratings, promotions, or development calls?
  • Who have you seen do manager enablement well, and what made it stick?
7:45pm

Peer EXchange #3 - Operating Model, Not Tool Stack: Building AI Upskilling Infrastructure That Lasts.

73% of organizations invest in AI upskilling, but no single approach breaks 30% adoption, and there's no consensus on who owns the work: managers (24%), the employer (22%), technology providers (22%), or individuals themselves (20%). Meanwhile, the market has spoken about what it values. Quality control beats coding. The scarcest, premium-commanding skills, like AI safety and governance, output evaluation, and workflow redesign, are exactly the ones piecemeal training doesn't build. You can't buy your way into AI transformation. You have to build it into job architecture, compensation bands, and L&D pathways.

Table Prompts: 

  • Which upskilling investments have actually changed behavior at your organization, and which just checked a box?
  • If judgment, governance, and quality control are the premium skills, what should your L&D priorities be next year?
  • What would it look like to reward the AI behaviors you value, in pay, promotion, and recognition, starting this cycle?
8:10pm

Dessert & Intentional Networking

We close the formal program, but the best conversations often continue here. Compare notes, exchange contact information, and solidify the relationships that will extend well beyond tonight. Leave sharper, better connected, and more strategically armed than when you arrived. Keep marching, my friend. We've got you.

Additional Benefits

More than networking. A full learning experience of value.

SHRM & HRCI Recertification Credits

Earn credits while engaging in executive-level, operator-focused discussions.

Complimentary Transportation

Attend with ease: Uber voucher plus on-site comped valet parking.

Team Advantage

We typically hold 2–3 seats per company so you can bring a colleague and accelerate adoption together.

Gifts & Raffle

Every attendee receives a special gift, plus a chance to win Amazon gift cards.

Exclusive Leadership Network Access

Join our invitation-only executive community with resources, virtual peer exchanges, and ongoing leadership development.
Additional Benefits

Let's Raise the People Function — Together

The future of your organization will not be decided by strategy alone, but by how powerfully People and Finance align to execute it. Let's raise the ambition of the People function to match the ambition of the business — and build the kind of partnership that turns vision into results.
EX Leadership Network

Let's Raise the People Function — Together

Membership turns this one-time event into a full year of learning, connection, and growth with peers who are operating at your level.
  • First access to in-person Leadership Exchanges
    Confirmed access before public registration opens.
  • Monthly virtual peer exchanges
    Small-group sessions on the challenges you're navigating now.
  • Private member directory & introductions
    Curated connections to operators across roles, stages, and industries.
  • On-demand resource library
    Frameworks, templates, and playbooks from every EXchange and Masterclass.
  • Executive Masterclasses & roundtables
    Deep-dive learning with sitting CHROs, CFOs, and senior operators.
From the Room

Moments from past Leadership EXchanges.

A glimpse into the rooms where the real conversations happen.

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