Career Contessa

The conversations you avoid at work could be holding your career back. Harvard Business School faculty member and Unspeakable author Christina Wing shares how to navigate seven of the toughest workplace conversations—from asking for more to owning mistakes and talking about money.
You’ll learn:
How to ask for a raise, promotion, or more responsibility with confidence
What to say when discussing mistakes, job security, and personal challenges at work
Simple scripts to make difficult conversations less awkward and more productive

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Book: https://www.christinawing.com/book/
LinkedIn: https://www.linkedin.com/in/christina-r-wing/
Website: https://www.christinawing.com/

Career Contessa Resources
Book 1:1 career coaching session: https://www.careercontessa.com/hire-a-mentor/
Take an online course: https://www.careercontessa.com/education/
Get your personalized salary report: https://www.careercontessa.com/the-salary-project/

Sponsors:
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If you’re ready to launch your business before Black Friday, go to shopify.com/careercontessa to start your free trial.
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AI was supposed to make work easier—so why are we busier than ever? Lauren talks with Axios co-founder Roy Schwartz about why simplicity is becoming a career advantage and how to cut through the noise to focus on what actually matters.
You’ll learn:
How to identify and eliminate “toxic complexity” at work
How to use AI without creating more work and noise
A simple framework for doing more by doing less

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
LinkedIn: https://www.linkedin.com/in/royschwartz/
Book: https://www.penguinrandomhouse.com/books/813390/simplify-by-jim-vandehei-mike-allen-and-roy-schwartz/
Website: https://smartbrevity.com/

Career Contessa Resources
Book 1:1 career coaching session: https://www.careercontessa.com/hire-a-mentor/
Take an online course: https://www.careercontessa.com/education/
Get your personalized salary report: https://www.careercontessa.com/the-salary-project/

Sponsors:
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Think you need more discipline to reach your goals? Jia Jiang, bestselling author of Rejection Proof and Easy Discipline, explains why relying on willpower and working harder often backfires—and what to do instead.
You’ll learn:
Why traditional discipline doesn’t work for most people
How enjoyment can make ambitious goals easier to sustain
How to redesign your habits so progress requires less willpower

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Newsletter: https://blog.jiajiang.com/
Website: https://www.jiajiang.com/
Book: https://www.jiajiang.com/easydiscipline

Career Contessa Resources
Book 1:1 career coaching session: https://www.careercontessa.com/hire-a-mentor/
Take an online course: https://www.careercontessa.com/education/
Get your personalized salary report: https://www.careercontessa.com/the-salary-project/

Sponsors
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A bad manager can undermine your confidence, hurt your performance, and even derail your career. But what if quitting isn’t an option? Career coach and author Cathy Alfandre shares how to recognize a damaging manager, protect yourself while you stay, and create a strategic exit plan. Plus, learn how to spot red flags during the interview process so you don’t end up with another bad boss.
You’ll learn:
How to tell the difference between a demanding manager and a damaging one
How to protect your confidence and career when you can’t quit
How to spot manager red flags before accepting your next job

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Website: https://cathyalfandre.com/
Book: https://cathyalfandre.com/my-book/
LinkedIn: linkedin.com/in/cathyalfandre

Career Contessa Resources
Book 1:1 career coaching session: https://www.careercontessa.com/hire-a-mentor/
Take an online course: https://www.careercontessa.com/education/
Get your personalized salary report: https://www.careercontessa.com/the-salary-project/

Sponsors:
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If you’re ready to launch your business before Black Friday, go to SHOPIFY.COM/careercontessa to start your free trial.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Why do so many successful women still feel like they're falling behind—even after achieving the career milestones they once dreamed of? Executive coach and former Google leader Brooke Taylor explains the hidden "Success Wound" that keeps high achievers chasing the next accomplishment without ever feeling like it's enough. Learn how to break free from the cycle of burnout, perfectionism, and self-doubt while pursuing ambition that actually feels fulfilling.
You'll learn:
Why burnout, perfectionism, and imposter syndrome may be symptoms—not the real problem.
The five types of "Unfulfilled Achievers" and how to identify your own patterns.
How to cultivate "aligned ambition" so you can pursue big goals without tying your self-worth to your achievements.

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Brooke Taylor LinkedIn: https://www.linkedin.com/in/brooketaylor-coach/
Book: https://www.hachettebookgroup.com/titles/brooke-taylor/healing-the-success-wound/9780306836107/?lens=balance
Website: https://brooketaylorcoaching.com/

Career Contessa Resources
Book 1:1 career coaching session: https://www.careercontessa.com/hire-a-mentor/
Take an online course: https://www.careercontessa.com/education/
Get your personalized salary report: https://www.careercontessa.com/the-salary-project/

Sponsors
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