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39: How to Decide: Should I stay or should I go?
Should I stay or should I go?
This is a question many of my clients come to me with. You've invested years at your company, built strong relationships, and know how to do your job well. But something feels off. Maybe you've gotten too comfortable in your groove. Maybe the company culture has shifted. Or maybe you know deep down that you're ready for more.
Our client, Dorothy, a negotiations coach herself, found herself at this exact crossroads. She was working at a large Fortune 500 healthcare organization and knew it was time to move up—but couldn't see clearly whether that meant staying or leaving.
Through our work together, Dorothy overcame her fear, activated her network, and landed a VP role at a fast-growing company where she's now building a supply chain and procurement function from the ground up.
The best part? Her husband noticed she doesn't look stressed anymore—even though she has more work than before. That's the power of finding work that's truly aligned with who you are.
Whether you're stuck in a comfortable groove or wrestling with the stay-or-go question yourself, you'll find inspiration in Dorothy's story.
02:42 — What was really blocking Dorothy from getting the recognition she deserved (hint: it wasn't just the company)
04:42 — The program elements that helped Dorothy get clarity, including the networking strategy that opened up multiple opportunities
09:20 — How Dorothy landed a VP role at a fast-growing company and why she feels re-energized instead of burned out
14:13 — How Dorothy balances her bigger role while staying true to her feminine leadership style
19:49 — The book Dorothy recommends that explains why women struggle with people-pleasing and boundary-setting (and how to overcome it)
—
Register for the Free Executive Presence for Women Masterclass: The 3 keys to Increase Authority and Influence, happening live on Thursday, August 8 at 12 PST.
A replay will be available for those that register! https://zoom.us/meeting/register/tJAkdOsrDItGdHchQv1BXFozsGRUjL74xlK#/registration
—
🌟 FREE MASTERCLASS: Achieve Your VP Promotion: 3 Steps to Success in the Next Year
https://sistersmart.com/register-sil
—
✈️ FREE PASSPORT TO PROMOTION PRIVATE PODCAST: 7 STEPS TO GET PROMOTED FROM DIRECTOR TO VP
Get access to the Passport to Promotion Private Podcast
—
👩💻 APPLY FOR THE SISTERS IN LEADERSHIP PROGRAM
An 12-month coaching program for women leaders who want to rise up and fulfill their career potential and get promoted from director to VP
Join Sisters in Leadership to Get Promoted to VP
—
💻 EXPLORE OUR LEADERSHIP COURSES
We offer a few leadership courses for you to begin sharpening your skills from meeting management to executive presence and productivity.
Sign Up for a Leadership Course
—
👋 CONNECT WITH JILL
🌐 Website: https://sistersmart.com/
🎥 YouTube: https://linktw.in/uWD3ko
💼 LinkedIn: https://www.linkedin.com/in/jillavey/
View all episodes
By Jill AveyShould I stay or should I go?
This is a question many of my clients come to me with. You've invested years at your company, built strong relationships, and know how to do your job well. But something feels off. Maybe you've gotten too comfortable in your groove. Maybe the company culture has shifted. Or maybe you know deep down that you're ready for more.
Our client, Dorothy, a negotiations coach herself, found herself at this exact crossroads. She was working at a large Fortune 500 healthcare organization and knew it was time to move up—but couldn't see clearly whether that meant staying or leaving.
Through our work together, Dorothy overcame her fear, activated her network, and landed a VP role at a fast-growing company where she's now building a supply chain and procurement function from the ground up.
The best part? Her husband noticed she doesn't look stressed anymore—even though she has more work than before. That's the power of finding work that's truly aligned with who you are.
Whether you're stuck in a comfortable groove or wrestling with the stay-or-go question yourself, you'll find inspiration in Dorothy's story.
02:42 — What was really blocking Dorothy from getting the recognition she deserved (hint: it wasn't just the company)
04:42 — The program elements that helped Dorothy get clarity, including the networking strategy that opened up multiple opportunities
09:20 — How Dorothy landed a VP role at a fast-growing company and why she feels re-energized instead of burned out
14:13 — How Dorothy balances her bigger role while staying true to her feminine leadership style
19:49 — The book Dorothy recommends that explains why women struggle with people-pleasing and boundary-setting (and how to overcome it)
—
Register for the Free Executive Presence for Women Masterclass: The 3 keys to Increase Authority and Influence, happening live on Thursday, August 8 at 12 PST.
A replay will be available for those that register! https://zoom.us/meeting/register/tJAkdOsrDItGdHchQv1BXFozsGRUjL74xlK#/registration
—
🌟 FREE MASTERCLASS: Achieve Your VP Promotion: 3 Steps to Success in the Next Year
https://sistersmart.com/register-sil
—
✈️ FREE PASSPORT TO PROMOTION PRIVATE PODCAST: 7 STEPS TO GET PROMOTED FROM DIRECTOR TO VP
Get access to the Passport to Promotion Private Podcast
—
👩💻 APPLY FOR THE SISTERS IN LEADERSHIP PROGRAM
An 12-month coaching program for women leaders who want to rise up and fulfill their career potential and get promoted from director to VP
Join Sisters in Leadership to Get Promoted to VP
—
💻 EXPLORE OUR LEADERSHIP COURSES
We offer a few leadership courses for you to begin sharpening your skills from meeting management to executive presence and productivity.
Sign Up for a Leadership Course
—
👋 CONNECT WITH JILL
🌐 Website: https://sistersmart.com/
🎥 YouTube: https://linktw.in/uWD3ko
💼 LinkedIn: https://www.linkedin.com/in/jillavey/