Career Conversation Newsletter 9/26/25
Over the last several weeks, If I haven’t been training for the Chicago Half Marathon (humble/terrified brag🏃🏽♀️🫣), I’ve been hosting conversations with leaders who are shaping responses to the radical shifts in work.
The old playbooks aren’t holding. Careers, teams, and companies are being redefined in real time. I’ve been tracking the signals and want to share a few standouts — plus an invitation to join the next conversation.
You’re Invited: Next Career Conversations Live
📅 September 17 - Noon CST
🎙️ Stop Waiting for Your Cookie: The Hard Truth About Promotions
I’ll be joined by Jennifer Jones, CMO at TIDI Products, for a candid conversation about why advancement isn’t about tenure — it’s about readiness, visibility, and the problems you’re trusted to solve.
👉 Register
The Reskilling Revolution
This week, Kelly Hoppesch and I co-hosted a Lunch & Learn with Matt Moog (CEO, CareerBird) and Futurist Rishad Tobaccowala (author of
Rethinking Work). We gathered HR leaders to dig into the transition from resumes and career ladders to skills and career portfolios.
💡 Companies are behind on role architecture and skills mapping.
💡 Building frameworks is slow, costly, and erodes trust.
💡 The future of work will look less like static jobs and more like music or film production — project-based, skills-driven, fluid.
📚 Resources from Rishad worth exploring:
Substack
✨ Bonus: Matt offered attendees a free test of CareerBird —
His new platform automates job architecture, skill-based job descriptions, and transparent career paths. I’m happy to make an intro if you’d like to explore it for your organization.
Professional Services CMO/CRO AI Roundtable:
Together with Jeff McKay, Founder & CEO of Prudent Pedal, I co-hosted a roundtable on how AI is reshaping marketing, sales, and service delivery.
3 fast takeaways:
No one’s “ahead.” Firms are investing, but operating models are still catching up.
Buyers want speed and value — but trust still comes from people.
Orgs are shifting: flatter structures, “T-shaped” talent, reskilling at scale.
Big thanks to Connor O’Halloran at Marsh for hosting.
Recruiting Win Spotlight
A recent placement at Talentfoot reminded me why I love executive search. Congratulations to Jeremy Baras on this new chapter, and to Camille Fetter for her vision.
This is the kind of work I thrive on — aligning talent with strategy, connecting dots that accelerate both careers and organizational growth.
Next Week:
I’ll be joining peers at the Fractional People People IRL Conference.
Excited to reconnect with the HR leaders who are on the frontlines of the future of work. I’ll share insights in my next newsletter.
Personal Note: Half Marathon Lessons 🏃♀️
This weekend I’m running my first half-marathon after 125 miles of training. What kept me moving: my daughter’s encouragement, a solid playlist, Brooks shoes, protein bars, and the Nike Run Club app.
Coach Bennett’s reminder sticks with me: “It’s about running… and it’s about more than running.” Same with careers — the work is the work, but it’s always about more than the work.
Blog coming soon with lessons (and songs) that push past the moment.
Connecting:
The pace of change isn’t slowing down. My work — in coaching and recruiting — is not just to help leaders adapt, but to lead the creation of the next iteration of the world of work.
How to engage:
📩 Book a free 30-minute coaching call
🤝 Start a recruiting conversation
