Managing Up with Challenging Bosses - WIMDI Interactive Webinar
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In 2026, The WIMDI Speaker Series is inviting engaging speakers each month to give interactive talks on topics that help women kill it at work.
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Welcome to Talk 1 of 13 - Managing Up with Challenging Bosses
Managing your career growth can be an absolute delight if you have a skilled manager that you get along with. But if your manager is…a little more difficult? Well, yikes.
Challenging bosses present a big obstacle to your success. It can be hard to get your achievements recognized, difficult to get your ideas heard, and almost impossible to perform and grow.
Even though it’s tempting to minimize your interactions with managers who drive you to distraction, It’s essential to your long-term career prospects to learn how to manage up so you can turn your most challenging leaders into supportive allies.
This talk will focus on how to effectively manage up when dealing with difficult, reactive, or tricky leadership.
We’ll cover:
- The 5 most common types of challenging bosses (and how to handle them!)
- How to speak up and self-advocate while maintaining your professionalism
- Strategies for diffusing conflict and creating emotional distance with difficult personalities
- When & how to turn your challenging manager into your biggest advocate
The goal of this talk is to give attendees practical tools and emotional clarity for navigating tough leadership dynamics, so they can advocate for themselves, stay in integrity, and move forward with purpose.
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Mary Connelly
Mary Connelly transforms high-performing professionals into influential leaders who advance their careers without sacrificing their authentic selves. Drawing from her proven background in media and sales management, Mary partners with senior executives at industry giants like Amazon, PepsiCo, AbbVie, and Hyatt Hotels, as well as ambitious leaders at high-growth startups.
Her coaching approach cuts through corporate noise by combining emotional intelligence with practical strategy. Whether navigating complex leadership transitions, mastering high-stakes communication, or accelerating career momentum, Mary's clients don't just succeed—they do it on their own terms.
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Attendance Notes:
- Gender:
This event is open to individuals of any gender identity. - Code of Conduct:
By Attending this event, you agree to adhere to WIMDI's code of conduct, which you can find at wimdi.com/code-of-conduct-and-policy. - Privacy, Photography and Recording*:
Online WIMDI events use Zoom, and we will be recording this event in the hopes of eventually releasing replays of the speaker portions of our events. As such we cannot guarantee that no photos, screenshots, or recordings will be taken of you during the event by event organizers or by other attendees. We love it when our members connect at our events using both video and audio, but we understand if our members prefer to participate with their video turned off to preserve (more of) their privacy.