Managing Up with Challenging Bosses

Managing Up with Challenging Bosses – Video

by Angela McConnell

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.

Talk Outline:

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.

Mary Connelly

Executive Coach & Founder, Mary Connelly Consulting

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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