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What Leadership Actually Looks Like — A Conversation with Ron Thomas

Some conversations stay with you long after the recording ends.

THE CEO SERIES with Ron Thomas repeats can be seen on YouTube
THE CEO SERIES with Ron Thomas repeats can be seen on YouTube

Last week I had the pleasure of joining Ron Thomas on The CEO Series — a weekly conversation he has hosted for years with leaders across industries, continents and disciplines. Ron and I go back to our time at Martha Stewart Living Omnimedia, where he served as VP of Human Resources and I worked on the production team. We were part of a company that, at its best, was a masterclass in building something from a clear creative vision and surrounding it with people who believed in the work.


Talking to Ron always brings me back to what leadership actually requires — not the polished version, but the real one. The kind that shows up when things are hard.


We talked about what it means to develop the next generation of leaders. Not just mentor them in the traditional sense — passing down wisdom from a safe distance — but genuinely invest in their visibility, give them room to lead, and let them make decisions that matter. Ron describes his approach to mentoring through three words: visibility, vulnerability and

velocity. Get people seen, be honest about your own failures, and push them to move.


We also talked about Heidi Diamond, who passed away in December. Heidi was President of Television at Martha Stewart Living during one of the most turbulent periods in that company's history. She held the television division together through circumstances that would have broken most people — and she did it by being transparent with her team, by communicating clearly, and by refusing to let adversity define the outcome. She described her own experience as days when even her eyelashes hurt. And yet she led.

That quality — the ability to hold a team together when the ground is shifting — is what Ron and I kept coming back to. It is not a skill you learn in a workshop. It is built through experience, through watching others do it, and through being willing to be seen struggling while you figure it out.


What I took from the conversation is something I think about often in my own work with creative professionals: the people who become great leaders are rarely the ones who had everything figured out. They are the ones who stayed in the room, stayed honest, and kept developing — themselves and the people around them.


If you want to find your own Creative Signature — the quality that runs through everything you do — it often starts by looking back at the moments when you led under pressure. What did you do? What did you protect? That is where your signature lives.

Personal Branding for Creative Entrepreneurs is available now. Book a Creative Signature Session at caliativity.com/book-online Use code THECEOSERIES20 for 20% off your first session.


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