Can AI Replace Kaye?
By Mitchell Schuckman, PCC | Executive Coach + Founder, The Schuckman Group LLC
When I started my own practice, one of the things I worried about most was how I would manage without the right hand person I’d worked with at a large professional services firm. She knew my calendar, my clients, my colleagues, my priorities, and probably a few things about me that I hadn't figured out myself. I’ll call her Kaye, but she knows who she is.
I was excited about building a business of my own. I was also very aware that I would be doing it without someone I had depended on for years. Finding a way to replace that support has been on my mind ever since.
She Knew the Questions Before I Did
Remember The Devil Wears Prada? Meryl Streep plays Miranda Priestly, the formidable fashion magazine editor, and Anne Hathaway plays Andy, her assistant.
As Andy learns her job, she becomes increasingly capable of anticipating Miranda's needs. She understands the people, the personalities, the priorities, and the details that mattered.
Kaye did something similar for me.
She was particularly good at anticipating the questions I might be asked and helping me consider how I should answer them. Sometimes this happened before a meeting. Sometimes it happened during one, when she would quietly remind me of a relevant fact, a previous conversation, or something about the person asking the question.
She helped me keep my head in the game.
What made her so valuable was her understanding of the people involved. She knew me, she understood the people I worked with, and she recognized what each situation required. I could walk into a meeting better prepared because she had helped me think through what might happen.
And when something unexpected happened, she was often one step ahead of me.
Starting My Own Practice Changed the Equation
As my business was starting, hiring someone like Kaye felt like a high-priced luxury. That is a practical reality, but as my business grows, it leaves me with a void.
I love the variety of my work. I coach executives, help professional services firms compete for major engagements, and work with leadership teams on growing their businesses. There are relationships to maintain, conversations to prepare for, sessions to design, and commitments to keep across all of it.
I have been desperate for that right-hand person. Someone who understands what I am trying to accomplish and can help me stay on top of everything involved.
That need is a large part of what has drawn me into AI. I have been using it to help me manage the work, and it helps. There are things Kaye did that AI can do even better. In fact, my wife sometimes calls ChatGPT and Claude my “friends”.
I want to acknowledge that plainly, because my appreciation for Kaye hasn't made me sentimental about every task she performed. I am quite willing to let technology do many things even better.
The Tool Keeps Getting Better
I am working hard to build an AI chief of staff. I have been teaching it about my business, my projects, my commitments, and how I approach decisions. I keep testing it, finding the gaps, and trying to make it more useful.
When it misses something, I want to understand why. When it makes a useful connection, I want to make that happen more consistently. I want it to become better at helping me prepare and recognizing what deserves my attention.
There are frustrations, and there is progress. I am putting the effort into this because I need the help and can see enough value to keep working at it.
As the tool improves, though, I keep coming back to Kaye.
I can look at an individual task and decide whether the system handled it well. I can assess whether a reminder was useful or whether preparation helped me enter a conversation with more of the relevant information in mind.
Deciding whether it can replace Kaye for me is proving harder.
Will I Have My Right Hand Back?
I have been asking myself what I actually depended on. How much was the work Kaye did? How much was the fact that another human being was doing it, someone who knew me and understood the people around me?
I am going to keep building my AI-based tool. I need the support, and I want to see how good I can make it. Every improvement gives me another reason to continue.
But I have realized that I am asking two questions as I work. Can I build a tool that does what I need a chief of staff to do? And if I succeed, will I feel that I have my right hand back?
I am increasingly optimistic about the first question. The second brings me back to what it felt like to have Kaye beside me. Another person was paying attention, bringing her own judgment, and taking an interest in how things turned out.
There are things AI already does better, and I expect that list to grow. Even so, I suspect that however good I make this tool, I will still miss having a person beside me.
I may eventually have all the help I need. I think I will still miss Kaye.