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Welcome back, Trailblazers. Today’s episode hits different. Tiffany Benitez and Jordan Franklin are joined by certified leadership coach Lisa Stryker, who’s here to talk about the moments most people skip in their highlight reel, confusion, redirection, and the stretch between doing the work and actually leading.
Lisa opens up about entering full-time work later than most, getting handed a high-visibility role, and feeling totally lost in it. That experience led her to a deeper question: Why is it so hard to go from being a great contributor to a confident leader? The answer turned into a mission. “I wanted to be a leader so badly. I just had no idea what that really meant.”
We dig into authenticity, not the filtered version, but the one rooted in values and intention. Lisa explains how understanding who you are at your core helps you lead from a place that’s real, even when you’re not feeling your best. And if you’ve ever heard that voice saying “don’t brag”, this episode is a must. Lisa reclaims the word with her BRAG method, Boldly Recognize Achievement and Growth, and gives practical ways to advocate for your work without sounding, well, annoying.
You’ll also hear why visibility matters just as much as mentorship, and why stretch roles, even the ones you don’t feel fully ready for, are where real growth lives. “Don’t think you’re wrong just because they disagree with you,” Lisa says. That one’s a gut check.
Here are the key takeaways:
(2:13) The authenticity equation
(3:23) Managing emotions in leadership
(4:23) From doer to leader
(8:39) Being right isn’t always popular
(10:37) Brag = boldly recognize achievement and growth
(11:31) Speak on it or stay invisible
(13:14) Stealth promotion over self-promotion
(17:05) Authenticity is holding the line
(19:25) Stop playing safe with promotions
(20:58) Hiring for potential, not perfection
(22:46) Finding mentorship the organic way
(25:54) When mentorship isn’t the right fit
(27:24) From comparison to claiming influence
So if you’ve ever played small, waited to be picked, or second-guessed your impact, this one’s for you. Tune in, take notes, and let this conversation push you toward your next bold move!
About Lisa Stryker
Lisa Stryker is an executive coach and the founder of Stryker Coaching & Communications. She works with mid and senior-level professionals to help them move from behind-the-scenes roles into visible leadership positions. With a background in corporate communications and over 25 years of experience, she supports clients through one-on-one coaching and group training. Lisa is certified by The Life Coach School, the John Maxwell Team, DISC, and DDI.
Connect with Lisa:
About Tiffany Benitez & Jordan Franklin
Tiffany Benitez leads Data Governance at Compass Group USA, ensuring data quality, integrity, and compliance across all business units. She is passionate about driving data excellence and advancing women in tech and STEM.
Jordan Franklin, CEO of Gumption and Stratice, is revolutionizing the job market with behavioral AI, making talent acquisition efficient. For three years, she's been celebrated as a top staffing influencer.
Connect with Hosts:
Tiffany’s LinkedIn
Jordan’s LinkedIn
Disclaimer
This podcast is for informational purposes only. The content should be taken as something other than professional advice. Listeners are encouraged to consult with professionals regarding specific situations or concerns.
Welcome back, Trailblazers. Today’s episode hits different. Tiffany Benitez and Jordan Franklin are joined by certified leadership coach Lisa Stryker, who’s here to talk about the moments most people skip in their highlight reel, confusion, redirection, and the stretch between doing the work and actually leading.
Lisa opens up about entering full-time work later than most, getting handed a high-visibility role, and feeling totally lost in it. That experience led her to a deeper question: Why is it so hard to go from being a great contributor to a confident leader? The answer turned into a mission. “I wanted to be a leader so badly. I just had no idea what that really meant.”
We dig into authenticity, not the filtered version, but the one rooted in values and intention. Lisa explains how understanding who you are at your core helps you lead from a place that’s real, even when you’re not feeling your best. And if you’ve ever heard that voice saying “don’t brag”, this episode is a must. Lisa reclaims the word with her BRAG method, Boldly Recognize Achievement and Growth, and gives practical ways to advocate for your work without sounding, well, annoying.
You’ll also hear why visibility matters just as much as mentorship, and why stretch roles, even the ones you don’t feel fully ready for, are where real growth lives. “Don’t think you’re wrong just because they disagree with you,” Lisa says. That one’s a gut check.
Here are the key takeaways:
(2:13) The authenticity equation
(3:23) Managing emotions in leadership
(4:23) From doer to leader
(8:39) Being right isn’t always popular
(10:37) Brag = boldly recognize achievement and growth
(11:31) Speak on it or stay invisible
(13:14) Stealth promotion over self-promotion
(17:05) Authenticity is holding the line
(19:25) Stop playing safe with promotions
(20:58) Hiring for potential, not perfection
(22:46) Finding mentorship the organic way
(25:54) When mentorship isn’t the right fit
(27:24) From comparison to claiming influence
So if you’ve ever played small, waited to be picked, or second-guessed your impact, this one’s for you. Tune in, take notes, and let this conversation push you toward your next bold move!
About Lisa Stryker
Lisa Stryker is an executive coach and the founder of Stryker Coaching & Communications. She works with mid and senior-level professionals to help them move from behind-the-scenes roles into visible leadership positions. With a background in corporate communications and over 25 years of experience, she supports clients through one-on-one coaching and group training. Lisa is certified by The Life Coach School, the John Maxwell Team, DISC, and DDI.
Connect with Lisa:
About Tiffany Benitez & Jordan Franklin
Tiffany Benitez leads Data Governance at Compass Group USA, ensuring data quality, integrity, and compliance across all business units. She is passionate about driving data excellence and advancing women in tech and STEM.
Jordan Franklin, CEO of Gumption and Stratice, is revolutionizing the job market with behavioral AI, making talent acquisition efficient. For three years, she's been celebrated as a top staffing influencer.
Connect with Hosts:
Tiffany’s LinkedIn
Jordan’s LinkedIn
Disclaimer
This podcast is for informational purposes only. The content should be taken as something other than professional advice. Listeners are encouraged to consult with professionals regarding specific situations or concerns.