These days my father shuffles around the house in the shape of an upside-down letter J. His conversational contributions are verbal jazz. Is he in there? It depends. His presence of mind is like the sun and, every day, depending on the weather, the visibility’s different. Sometimes he wakes up enveloped in mist, but unannounced, for around three minutes, the skies clear up and I can make him laugh. Other days the clouds are many and he shines in and out of reality according to some mysterious schedule nobody’s got a copy of.

My mom has gone from merely supervising his morning coffee to spending long minutes quizzing him as to whether a cup of coffee is what he actually wants (he's used the word "squirrel" and "handsaw" in the request, so all bets are off). She must now identify the need, prepare the coffee, and deliver it to his shaky hands. She reminds him how close the cup must be to his lips for drinking. She reminds him to swallow. When I step in to supplement her caretaking, she says no, frantic—she doesn’t know how to explain it all, and it would take too long, anyway. Delegation was never her strong suit, but she's forgotten completely what it's like to share work. She's the leader here, and it's lonely.

Simplify's audio engineer sends me a video. His tiny child stands on a chair before a floury cutting board. He is making pão com chouriço (a kind of Portuguese pepperoni bread) from scratch. I am enthralled by how exactly his little hands place each slice of meat, how neatly and confidently he folds the dough. I am even more impressed by his father's gentle coaching. Off camera, I hear him say, "Fold here… pull it over… a little more…there! That's perfect. Good." He does not leap in to do it for his son. Instead, he talks him through—adjusting, suggesting, praising at the right moment. If this isn't good leadership, I don't know what is.

I sit down with my mom, braced to tackle a 27-thread chain of emails from her lawyer. Each one contains multiple paperwork requests or processes to start or calls to make. It is no wonder she is overwhelmed. I take a deep breath. I comb through each of the messages, creating an itemized list of next actions. After a couple of hours, we have a strategy for getting her to the end of a grueling Medicaid application process and start making calls. In my own way, I'm leading now, too.

Even if your job has no classical "leadership" responsibilities, chances are you're doing it anyway. You're doing it when you figure out what actually needs to happen and in what order. You're doing it when you notice someone is struggling before they say so. You're doing it when you resist the urge to just do the thing yourself and instead walk someone else through it. Fold here. Pull it over. A little more. Perfect.

The moment you step forward to be custodian of an outcome, serving and honoring the people attached to it, you're leading.

And so, I thought all of us could use a little help and clarity with this very important role—which brings me to today's guest, Deborah Caulet.

Having established a practice as a coach and worked in People & Culture at organizations from L'Oréal to smaller startups, Deb is an expert in leaders’ everyday challenges and breakthroughs. She's also an expert in rituals—which relates to her work in leadership way more than you might initially imagine. After all, what is a functioning work culture if not a series of rituals that binds people together?

New leaders come to Deb for all kinds of things. She helps them learn to lead colleagues who were once their peers, how to shift from individual contributor to leader, how to distribute their tasks so their whole team can move faster. At the root of it all, though, is one subtle, disorienting truth about leading that she names better than anyone I've heard:

In this episode, you'll learn Deb's CLEAR framework for having tough conversations, how to start delegating and stop being your own bottleneck, and her take on the most important qualities of a leader in 2026—the age of AI. Bonus: you'll also learn how to fire someone. Eek!

Deb doesn’t have a book (yet!), but if if you could use a hand with having tough conversations, she’s got a free 7-day offering you can find here, and you can find out more about working with her right over here.  

Listen. Learn. Lead. (the natural cultural heir of Live, Laugh, Love?). 

‘Til soon,
Caitlin

P.S. Please share with a friend you think will enjoy this episode. It’s the best way you can help Simplify stick around! Also, let me know what you thought by replying here or writing to me and Ben at [email protected]. 

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