Sheila O'Sullivan teaches the skill AI can't do for you

Sheila O'Sullivan · Published November 10, 2026

Startup operator Sheila O'Sullivan teaches a Maven course on the communication skills that matter more as AI takes on technical work, and builds her own AI tools for her business and her home.

Sheila O'Sullivan has held VP, CSO and COO roles at fast-growing companies and helped scale a startup to a sale. These days she's focused on something she never gets tired of talking about: why your perfectly clear, perfectly reasonable message gets misread.

Her bet on where careers are headed is clear. "As AI agents take over more technical work, how you communicate with humans is quickly becoming your biggest non-AI career differentiator," she wrote.

Communication Comfort Zones

Sheila teaches a framework she calls Communication Comfort Zones through a live course on Maven and private workshops for businesses and community groups like Chief. The idea is that most of us get comfortable speaking in the way that works for us, and speaking another way feels uncomfortable. Communication issues in our relationships become especially challenging when we subconsciously believe our own way is the "right" way. The fix is letting go of that mental model and understanding and practicing how other people want to hear information.

She learned this the hard way. When she became a manager, her feedback landed well with some people and shut others down, and she'd leave meetings sure she was crystal clear only to find half the team was confused. At first she thought the problem was them. Then she realized it was her.

"Effective communication is not simply charisma that someone is born with," she wrote. "It's a skill you can learn."

Building with AI

Sheila isn't just talking about AI from the sidelines. She recognizes how radically it changes how to grow a business. Two decades of building taught her that while the right concept must be there to start, it takes a thousand more ideas to turn it into a commercially viable business. The work she loves is generating those ideas, testing their effectiveness, and building out the people, processes and technology to turn them into revenue. AI makes building and testing ideas and supporting their implementation happen much faster.

Her first AI concept-to-reality was her own Communication Comfort Zones practice chatbot for clients, built with help from AI teacher Lori Mazor. "Would I have tried to build my own chatbot for clients if I hadn't met Lori Mazor? I'm not sure. But I do know that I did it with her help," she wrote. The experience gave her the confidence to create more tools, including a custom CRM, an automated communication style quiz and profile generation workflow, and a content pipeline management system.

"In the late 2010s, building the custom CRM for our enterprise took two dedicated developers and months of work. This year, I built the base CRM for Communication Comfort Zones using Claude, Notion, and Instinct in less than a week."

Sheila also obsesses over streamlining work at home. Her grocery assistant AI tool lets her family request items through an iPhone shortcut and delivers them to an online grocery list, where she can choose the source (Trader Joe's, Costco, the local grocery store) and check off items when they're purchased. She also built an invoice processing system to keep track of itemized expenses for her son's burgeoning go-kart racing career.

It becomes a bit of a dopamine fix. I love solving problems, and I have to watch that I don't spend too much time solving problems for fun instead of impact.

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