Free Business Topics in Chicago

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  • Read the Room: Frameworks for Multigenerational Communication

    Gabby Rosely, Consultant, Gabby Rosely LLC

    The US workforce is the most age-diverse it's ever been, with Gen Z now outnumbering Boomers for the first time. Yet most teams are still struggling with the same old generational friction.
    I'm gonna be real with you: generational cohorts are just the starting point. MORE >

    You're not actually going to walk around asking coworkers their age so you can put them in a box. That would be weird. If you know someone’s age but still make assumptions about them, the point is totally missed.

    The POINT is: learning about how worldviews & values are shaped, how to ask the right questions, read the room, and connect with people who think completely differently than you do. This keynote / workshop gives you the tools to do that - with your team, with strangers, with prospective clients - so you stop second-guessing yourself and start building actual trust.

    “Staying in Your Own Lane DOESN’T work in Business” moves beyond tired stereotypes to unlock what actually motivates Baby Boomers, Gen X, Millennials, and Gen Z.

    What You'll Experience:
    - Understand the real values and communication preferences driving each generation
    - Interactive exercises that build empathy and reveal hidden strengths
    - Practice the conversations you've been avoiding, like, giving feedback, addressing conflict, motivating people who seem checked out
    - Leave with a personalized strategy to connect authentically with every team member

    The real result? You stop tiptoeing. Your team stops living on islands. You build the kind of trust that makes people actually want to work together. Generational differences become your greatest advantage.

    Why me? I'm a Gen Z leader who managed teams across all four major generations at age 21. I also totally face-planted at first, thinking I could "stay in my lane," do things my way, and it'd all work out. Spoiler: it didn't. I had to learn this stuff the hard way, in the face of everyone doubting me because of my age. (Trained by Gallup-certified Strength Advisors & MetaPerformance Institute, but honestly, the real credential is that I've lived both sides.).

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  • The Culture Shift Starts Within: Tackling the Hidden Barriers to Collaboration

    Anthony Bolden and Charles Cammack, Co-founders, BridgeWork LLC

    Dr. Shirzad Chamine’s groundbreaking research introduces the concept of “Saboteurs”—internal voices that once helped us navigate real and perceived threats in childhood. While these mental patterns originally served as protection, they often persist into adulthood, operating as unseen forces that shape how we think, feel, and respond. MORE >

    Over time, these Saboteurs become embedded in our neural pathways, creating automatic reactions that can “hijack” our behavior in moments of stress or challenge.

    In this session, your team will learn to recognize and understand these patterns, identify their own Saboteurs, and develop practical strategies to build greater self-awareness. The goal is simple but powerful: to help individuals show up as assets rather than obstacles to their teams and the broader mission.

    By equipping your people with this insight, your organization takes a meaningful step toward becoming more people-centered—grounded in self-awareness, stronger collaboration, and more intentional impact.

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  • Master Networking for your business

    Dan Gelfond, Former Steven Spielberg Project Interviewers, Personal History Interviews

    Join Dan Gelfond, a master networker with 28+ years of experience building his business almost entirely through networking. As moderator of the Northbrook Chamber’s “First Friday” networking meeting for the past 25 years (averaging 110 attendees monthly), Dan brings proven, practical strategies you can use immediately.
    What you’ll learn:
    Clear, actionable do’s — and even more important don’ts — for effective networking
    How to craft and perfect a compelling elevator pitch MORE >

    Practical tips to maximize your ROI from every networking opportunity
    Format:
    Fun, interactive seminar tailored for companies or organizations with sales staffs.
    Hands-on exercises, real-world examples, and time for Q&A.

    For companies with sales staff in multiple locations, seminar can be conducted via Zoom.

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  • You Never Said Anything: Why High Performers Get Passed Over

    Rosie Zilinskas, Keynote Speaker | Certified High-Performance Coach, No Woman Left Behind

    High-performing women in corporate roles deliver real results every day. And yet, many of them are still not being recognized and rewarded at the level they have earned. MORE >

    It is not because they lack talent. It is not because they lack confidence. It is because of the Articulation Gap: the distance between the impact they create and the impact leadership recognizes and rewards.

    In this keynote, Rosie Zilinskas reveals why strong work alone does not lead to advancement, and what high-performing women can do about it. Drawing from over 30 years of corporate leadership experience, including Executive Vice President at AIG Private Client Group, Rosie delivers a practical, story-driven talk that resonates with women across industries and leadership levels.

    Her structured approach is built on three pillars:
    ~ Clarity: knowing your impact in measurable terms
    ~ Composure: delivering your impact when the pressure is on
    ~ Conviction: directing your impact to the people who make decisions about your career

    What attendees will walk away with:
    ~ A name for the invisible problem that has been stalling their careers
    ~ The ability to translate task language into impact language that leadership responds to
    ~ A clear, repeatable structure for articulating their value in performance reviews, leadership conversations, and interviews
    ~ The knowledge that they were never behind. They simply had not been taught how to say what they do in the language that gets recognized and rewarded

    Ideal for:
    ~ Mid-level to senior women in corporate roles (Director, VP, Senior Manager)
    ~ High-performing women in finance, insurance, and structured performance-driven organizations
    ~ Women's leadership summits and ERG events
    ~ Corporate learning series and leadership development programs
    ~ Association meetings and industry conferences

    Rosie Zilinskas is a keynote speaker, Certified High Performance Coach, and StoryBrand Certified Guide. She is the Incoming President of the NSA Illinois Chapter (July 2026) and host of the No Woman Left Behind podcast.

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  • Own the Interview: Preparation That Reduces Anxiety

    Rosie Zilinskas, Keynote Speaker | Certified High-Performance Coach, No Woman Left Behind

    Interviews do not have to feel overwhelming. This hands-on session gives you a practical system to prepare for any interview and show up feeling calmer, clearer, and more in control. The session also introduces free AI tools like ChatGPT for ongoing interview practice. No tech experience needed. Whether you are changing careers, preparing for a promotion, or navigating an unexpected job search, you will leave with a clear plan and renewed self-assurance. MORE >

    What attendees will walk away with:
    ~ How to build a Story Vault of accomplishments so you have clear, structured examples ready for any question
    ~ Confidence-building opening phrases to start strong and command attention
    ~ Three strategies for responding when you are unsure how to answer a question, so you never freeze or go blank
    ~ How to create a 90-Day Plan that signals readiness and forward thinking to a hiring manager
    ~ A simple pre-interview routine to manage nerves and stay grounded on interview day
    ~ Access to a custom AI interview practice coach for continued preparation after the session

    Ideal for:
    ~ Job seekers at any career stage
    ~ Career changers and professionals reentering the workforce
    ~ Mid-career professionals preparing for internal interviews or promotions
    ~ Anyone who feels anxious or underprepared walking into interviews
    ~ Libraries, workforce development programs, community organizations, and corporate learning events

    Presented by Rosie Zilinskas, a Certified High Performance Coach and former Executive Vice President who has sat on both sides of the interview table during 30+ years of corporate leadership at AIG Private Client Group.

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  • Mastering Modern Resumes with AI

    Rosie Zilinskas, Keynote Speaker | Certified High-Performance Coach, No Woman Left Behind

    Hiring managers spend 6 to 10 seconds scanning your resume. That is all the time you have to make an impression. This session covers what a modern resume looks like, what has changed in the current marketplace, and how to position your accomplishments around measurable results instead of task descriptions. You will also learn how to use AI to pull strategic keywords from job descriptions and tailor your resume for each role without starting from scratch. MORE >

    What attendees will walk away with:
    ~ A clear understanding of the five essential sections of a modern resume (header, summary, experience, education, skills) and when to include additional sections
    ~ How to write a professional summary that works like an elevator pitch
    ~ How to rewrite experience bullet points using measurable, results-oriented language
    ~ Practical tips for optimizing a resume for Applicant Tracking Systems so it does not get filtered out before a human sees it
    ~ A reusable resume structure and a simple system to keep it current

    Ideal for:
    ~ Job seekers who have not updated their resume in years
    ~ Mid-career professionals preparing for a new role or promotion
    ~ Career changers who need to reposition their experience
    ~ Anyone whose resume lists tasks instead of results
    ~ Libraries, workforce development programs, professional associations, and corporate learning events

    Presented by Rosie Zilinskas, a Certified High Performance Coach and former Executive Vice President with over 30 years of corporate leadership experience, including hiring, talent development, and learning and development at AIG Private Client Group.

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  • Optimizing Your Job Search with AI

    Rosie Zilinskas, Keynote Speaker | Certified High-Performance Coach, No Woman Left Behind

    AI can speed up your job search when you know how to use it strategically. This session goes beyond the resume and covers how to use free AI tools across every stage of the job search process, from applications to networking to interview preparation. You will learn prompts that save time while keeping your unique voice, and how to build a system that creates momentum without burning you out. MORE >

    What attendees will walk away with:
    ~ How to strengthen a LinkedIn profile, headline, and job descriptions with AI-generated improvements
    ~ How to write authentic outreach and networking messages that start real conversations
    ~ How to use AI to research companies, identify roles, and explore new career paths
    ~ How to build a Story Vault of accomplishments using the Problem-Action-Solution format
    ~ A simple weekly checklist and workflow to stay consistent and organized throughout the search
    ~ Ready-to-use ChatGPT prompts for every step

    Ideal for:
    ~ Active job seekers who want to work smarter, not harder
    ~ Professionals navigating a career transition or unexpected layoff
    ~ Anyone overwhelmed by the volume and complexity of a modern job search
    ~ People curious about AI who want a practical, hands-on introduction
    ~ Libraries, workforce development programs, community organizations, and professional associations

    Presented by Rosie Zilinskas, a Certified High Performance Coach, keynote speaker, and former Executive Vice President with over 30 years of corporate leadership experience.

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  • Brand Succession: The Marketing Playbook for Family Businesses in Transition

    Jennifer Fortney, Founder, Cascade Communications

    Your family business survived the hard part — building something worth passing down or selling. But when leadership transitions to the next generation or new owner, most companies keep the old brand out of loyalty to the founder. That loyalty can quietly work against the new leadership's vision, credibility, and growth as well as the direction of the company. MORE >

    Jennifer Fortney draws on 25+ years of brand and PR strategy to walk family business owners and next-generation leaders through the marketing blind spots that emerge during generational transition — and what to do about them.

    You'll learn:

    • the five warning signs your legacy brand is holding new leadership and the company back
    • a practical framework for honoring your history while building the future
    • and how to reposition your story for the customers, markets and key stakeholders

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  • Think Like a CFO: Financial Strategies Every Business Leader Should Know

    Jennifer Witter, Founder and CEO, Witter Enterprise Solutions, LLC

    Strong financial leadership is essential for every successful organization, not just those in the finance department. In this presentation, Jennifer Witter shares practical insights from the perspective of a CFO to help leaders better understand financial performance, cash flow management, and strategic decision-making. Participants will learn how to interpret financial information, identify key indicators that impact business health, and make more informed decisions that support growth and stability. MORE >

    This talk is designed for executives, entrepreneurs, and managers who want to strengthen their financial awareness and lead their organizations with greater confidence.
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  • AI for Business Leaders: What Executives Need to Know Now

    Jennifer Witter, Founder and CEO, Witter Enterprise Solutions, LLC

    Artificial intelligence is rapidly transforming how organizations operate, make decisions, and compete. This presentation provides business leaders and executives with a practical understanding of AI. What it is, how it works, and where it is already creating value in business functions such as finance, operations, marketing, and strategy. Participants will learn how AI can enhance data analysis, improve forecasting, increase operational efficiency, and support better decision-making. MORE >

    The session also addresses common misconceptions, risks, and ethical considerations, helping leaders understand how to responsibly adopt AI tools while maintaining human judgment and strategic oversight. This talk is designed for leaders who want a clear, practical perspective on how AI is shaping the future of business.
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