From First Job to the Top Job: Lisa Caswell on Navigating the Job Search

What does it really take to stand out in today’s job market, whether you’re fresh out of college, working toward a board position, or somewhere in between?

In this episode, Rose and Dana sit down with Lisa Caswell, an executive search expert with over 30 years at the top, including stints at Apple, Ariba, and IBM. Now at Spencer Stuart, Lisa opens up about what separates the candidates who thrive from those who stall.

This isn’t your typical career advice conversation. Lisa reveals why you should always be interviewing (even if you're not looking), how to make networking actually work for you, and the real reason most people fail to make the leap to leadership. She also gets brutally honest about the impact of AI, why boards say no, and how to define your personal value prop before someone else does it for you.

Whether you’re trying to break in, level up, or future-proof your career, this one’s full of practical insights.

Tune in to this episode as we explore:

(06:17) Career reflections and economic concerns

(07:07) Network, connect, and communicate early

(10:18) How AI is reshaping job skills and education

(15:02) Shifts in the job market

(18:04) Embracing fearless interviewing

(20:57) Know your boardroom value

(25:01) Board strategy in the tech world

(27:57) Advisory board pay and expectations

(32:19) Capability vs capacity

(35:41) Career modelling and personal validation

(38:20) How AI is being integrated into roles

(41:32) Strategic networking for board positions

Links mentioned in this episode:

Connect with Lisa on LinkedIn

The Career Playbook – Book

2024 U.S. Spencer Stuart Board Index

Career Advice: You Are the Brand

Preparing for a Board Opportunity

2024 U.S. Technology Spencer Stuart Board Index

Connect with the show:

Maestro Mindset LinkedIn Group

Maestro Mindset YouTube Channel