Illinois Search & Staffing Association upcoming events

2026 Midwest Staffing Conference (April 22, 2026)

Wed, 22 Apr 2026 14:00:00 GMT

Conference Hosts:

Illinois Search and Staffing Association

Wisconsin Association of Staffing Services

Michigan Association of Staffing Services

This highly anticipated 2-day event is designed for staffing professionals from all over the Midwest to come together and share their expertise, collaborate, and learn from industry leaders.

The Midwest Staffing Conference is an event for your entire team:

Owners / Managers / Sales Team / Recruiters / Emerging Leaders / HR

View the AGENDA for the 2026 Midwest Staffing Conference!

Click HERE

View the SPEAKER LINEUP for the 2026 Midwest Staffing Conference!

Click HERE

Attendance at the 2026 Midwest Staffing Conference

is approved for 7.5CE credits

REGISTER BY MARCH 1st FOR EARLY BIRD MEMBER DISCOUNT!

ISSA Members: Log in and register

WASS and MASS Members: Email your Director for discount code

NAPS Members: Email info@issaworks.com

Book Your Accommodations

The Hilton Chicago-Oak Brook Suites and Hilton Garden Inn Chicago-Oakbrook Terrace are located just steps from Drury Lane while the DoubleTree by Hilton Chicago-Oak Brook offers convenient shuttle service.

Hilton Chicago - Oak Brook Suites

(630) 941-0100 - Check Room Availability

Hilton Garden Inn Chicago-Oak Brook

(630) 941-1177 - Check Room Availability

Doubletree by Hilton Hotel Chicago-Oak Brook

(630) 472-6000 - Check Room Availability

ASA Staffing Law & Compliance Conference (May 07, 2026)

Thu, 07 May 2026 05:00:00 GMT

This highly focused event will deliver the answers you need on the hottest topics, such as immigration compliance, AI in recruiting, fraud protection, and much more. This year’s conference and expo takes place May 7–8 at the Grand Hyatt in Washington, DC.

From Rockstar to Leader: Questions That Make or Break the Shift (May 21, 2026)

Thu, 21 May 2026 18:00:00 GMT

From Rockstar to Leader:

Questions That Make or Break the Shift

The next generation of search and staffing leaders is eager to rise. But moving from top performer to effective leader is not simply a reward for strong performance. It is a high-stakes decision that requires different mindsets and strengths, and a clear-eyed look at what day-to-day leadership will ask of both the person stepping in and the leader making the call.

Designed for both emerging leaders and the senior leaders selecting them, this session explores the space between two critical questions: Should I step into leadership? and Should I promote this person?

Drawing on years of experience with advising dozens of succession decisions in the search industry, this webinar will help you make better decisions by distinguishing between performance and readiness, testing common assumptions, and clarifying what must be true before leadership becomes the right next move.

You’ll walk away with:

A practical framework for evaluating leadership decisions through business need, role fit, support, and tradeoffs
Strong questions for both rising leaders and senior leaders to ask before a promotion decision is made
Clarity on the difference between top performance and real leadership readiness
A grounded view of when the right answer is yes, not yet, or no

May 21, 2026 - 1PM CST

ISSA Members Free / Nonmembers $39

MEET THE SPEAKER

Annette Wehrli helps search & recruiting firm owners and leaders solve leadership, structure, and people challenges that prevent growth.

With 20+ years prior experience on MRI Network's corporate team leading organizational development consulting, executive coaching, succession planning, and learning development, Annette simplifies what's comlex and builds practical solutions that strengthen leadership, talent strategy, hiring, culture, and performance.

She's known for connecting the dots, asking questions that address and remove obstacles, building practical, relevant programs, and helping leaders be more intentional about their short- and long-term impact on people and business results.

ISSA Member Networking Event (June 01, 2026)

Mon, 01 Jun 2026 05:00:00 GMT

Why Sales Is Struggling (And It’s Not the Market): Leadership Blind Spots in Staffing (June 18, 2026)

Thu, 18 Jun 2026 18:00:00 GMT

The ISSA is proud to present the next virtual event in our Owners and Executives Series

Why Sales Is Struggling (And It’s Not the Market)
Leadership Blind Spots in Staffing

This 45 minute webinar is a straight shot of truth for staffing leaders who are tired of blaming “the market” for flat sales and shrinking pipelines.

Because the market is not the problem. The real issue is leadership.

In this session, Tiffany Scott pulls back the curtain on the uncomfortable realities most firms avoid. Vague expectations. Tolerated underperformance. Managers who coach softly instead of leading clearly. Sales teams with no real ownership, no strategy, and no edge.

You will learn:

Why “the market” is the most expensive excuse in staffing
How unclear expectations quietly kill performance
The cost of keeping the wrong people too long and why firing faster protects your culture
How to build real accountability without turning into a micromanager
Why transparency with your team is non negotiable in today’s environment
The role managers must play in building and enforcing strategy, not just reporting numbers
How to help sellers create a sales style that actually fits their personality
Why “our people” is no longer a differentiator and what leaders must do about it
How executives must own the firm’s edge in a crowded market

This is not a motivational talk. It is an operator’s perspective on what is actually broken inside most staffing organizations and how to fix it.

Attendees will walk away with a new lens on leadership, a sharper understanding of their own blind spots, and a clear framework for building sales teams that perform because they are led well, not just when the market is “good.”

MEET THE SPEAKER

Tiffany Scott is a 20-year staffing industry veteran and former Chief Operating Officer who helped scale a regional staffing firm from $10M to $190M in revenue. With 17 years of hands-on staffing leadership experience, she has built and led high-performing sales, recruiting, and operations teams across multiple markets and verticals. Her career has been defined by building systems that scale, developing leaders from the ground up, and driving growth through disciplined execution.

Today, Tiffany is the Founder and CEO of myScout, a prospect intelligence platform built exclusively for the staffing industry. myScout blends AI and human verified data to give staffing firms accurate, actionable insight into real decision makers inside target companies. Her mission is simple: help staffing leaders stop wasting time on bad data and start having better, faster, more profitable conversations.

Known for her direct, no nonsense leadership style, Tiffany speaks candidly about what it really takes to grow a staffing business in a modern market. She brings a rare mix of operator experience and forward-thinking innovation, helping firms rethink how they prospect, position, and scale in an industry that is changing fast.

Thank you to our event sponsor, Avionté!

2026 Midwest Staffing Owners and Executives Retreat (August 20, 2026)

Thu, 20 Aug 2026 05:00:00 GMT

Join us August 20-21, 2026 at the Q Center in St. Charles, IL

for the Midwest Staffing Owners and Executives Retreat -- an unparalleled opportunity for high-level leaders to exchange insights, challenge perspectives, and walk away with fresh strategies that drive real growth.

Your Hosts for the 2026 Owners and Executives Retreat:

Illinois Search and Staffing Association

Wisconsin Association of Staffing Services

Michigan Association of Staffing Services

Attendance at this event earns 6.0 CE Hours

toward ASA Certification

Thank you to our event sponsors!

Additional sponsorship opportunities are available

Email info@issaworks.com

Virtual Event - Why YOU? How Staffing Firms Become the Obvious Choice for Clients and Candidates (August 27, 2026)

Thu, 27 Aug 2026 18:00:00 GMT

In a staffing marketplace where speed, technology, and process are often assumed to be the differentiators, clients and candidates are quietly asking a more fundamental question: Why should I choose you?

This webinar invites staffing leaders, recruiters, and sales professionals to step back and examine what truly drives trust, loyalty, and long-term success. Drawing from decades of business leadership and relationship-driven sales experience, Maureen O’Brien – The Sales Sage™ and CEO of the Global Wisdom & Leadership Forum, explores why the most successful staffing firms stand out not because of what they offer — but because of how they show up.

Participants will be challenged to rethink differentiation through a human lens and to uncover the often-overlooked elements that influence client and candidate decisions in moments of uncertainty, change, and risk. This session moves beyond tactics to help staffing firms clarify and communicate what makes them genuinely choose-worthy in a crowded market.

At the conclusion of this webinar, the participant will be able to:

Identify the real factors that influence why clients and candidates choose one staffing firm over another — beyond speed, tools, or price.
Strengthen trust and credibility at every touchpoint by aligning leadership, communication, and relationship-building across the organization.
Clearly articulate their firm’s value in a way that feels human, confident, and differentiated — especially in competitive or uncertain environments.

August 27, 2026 - 1PM CST

ISSA Members Free / Nonmembers $39

MEET THE SPEAKER

Maureen O'Brien is a dynamic business leader, globally recognized keynote speaker, and bestselling author known for helping organizations build high-performing teams through trust, clarity, and human-centered leadership.

With more than 30 years of experience leading a multi-generational, service-based construction business, Maureen understands firsthand what it takes to attract talent, develop people, retain clients, and grow revenue in competitive, relationship-driven industries. She is the founder and CEO of O’Brien & Son, Inc., a company she has successfully led for over 38 years, and the founder and Managing Partner of the Global Women’s Leadership Forum®, where she partners with organizations to strengthen leadership at every level.

Maureen’s work sits at the intersection of leadership, sales, and resilience. Her expertise in Relationship Sales and Point of Light Leadership™ equipping staffing professionals to build stronger pipelines, deepen trust with clients and candidates, and lead confidently through uncertainty and change.

A Stage IV lymphoma survivor, Maureen brings a powerful, real-world perspective on resilience, decision-making under pressure, and what truly matters when the stakes are high. Her message resonates deeply with leaders and sales professionals navigating rapid change while still being expected to deliver results.

Maureen is the author of four bestselling books, the most recent, “26 Points of Light—Illuminating One Cancer Survivor’s Journey from Diagnosis to Remission.” All profits from the book go to cancer research and patient care. She is a recipient of the Dr. Martin Luther King Jr. Award, and she has been recognized as one of Illinois’ most powerful women. Audiences consistently describe her as insightful, grounded, and refreshingly real — a leader who speaks from experience, not theory.

ASA Staffing World (October 12, 2026)

Mon, 12 Oct 2026 05:00:00 GMT

The Future of Staffing: Driven by People, Powered by Tech

The staffing industry is being rewritten. Staffing World is the industry’s premier event where the community comes together to drive change. Attendees gain actionable strategies from leading experts, turn challenges into opportunities, and build connections that move careers and companies forward.

NAPS IGNITE 2026 Annual Conference (November 01, 2026)

Sun, 01 Nov 2026 05:00:00 GMT

For Information and Registration

Click Here

ISSA Annual Meeting and Holiday Event (December 03, 2026)

Thu, 03 Dec 2026 06:00:00 GMT