Gabby Rosely

Consultant, Gabby Rosely LLC

Free Business Speaker in Chicago

  • Staying in Your Own Lane Doesn’t Work in Business: Bridging Communication Gaps across Generations & Personalities

    TOPIC CATEGORY: Business

    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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  • What to Do when you have NO IDEA What to Do: Reconnecting to your Purpose

    TOPIC CATEGORY: Motivational

    You feel stuck, uninspired, unmotivated, & you're asking yourself - what do I do now? Maybe you're working a job you don't care about, maybe your relationship feels unfulfilled, maybe you're craving a new hobby... the point is, something is missing and you feel it - every single day. MORE >

    In this keynote / workshop, I break down the actionable steps (in the workshop we actually go through them together) to reconnect to your purpose, your gifts & talents, and how to take aligned action EVEN WHEN YOU DON'T feel like it, in the direction of your vision.

    When we feel stuck, it's usually a lot deeper than "what we're doing" & "what we're not doing" - this is an opportunity to connect to your heart, your dreams, & ground them into reality in ways that feel inspiring AND realistic.

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