The AI hype cycle is all contracts, code, and copy. But that’s not where the real founder advantage lives.
I’m a lawyer who advises startups and a founder myself. I’ve seen firsthand how AI can be far more than just a tool for automation or drafting legal documents. The real magic of AI is how it makes perspective accessible and interactive. It can challenge your assumptions, see patterns you’ve overlooked, and connect dots across hard data and soft signals like tone, personality, and organizational culture.
Used well, AI isn’t just a time-saver. It’s a partner in thinking smarter, spotting blind spots, and making better decisions.
Here are five ways I’ve seen founders, including myself and my organizations, unlock AI in less-than-traditional (but seriously effective) ways:
1. Play Devil’s Advocate to Stress-Test Your Ideas
Before you share a deck or strategy doc, run it through AI and tell it to think like an investor, regulator, or competitor. You’ll quickly see your idea from an angle you’d never pick yourself—usually the one your actual audience will.
I was drafting a regulatory document for the State Department regarding a client’s technology. We needed a favorable outcome quickly. I didn’t have time to waste with regulatory back and forth. I had ChatGPT pretend to be the regulators and review my document from a national security perspective. This allowed me to anticipate every hole that was about to be poked in my arguments. It also uncovered some seriously good policy arguments that I was totally unaware of. I got the fastest turnaround I’ve ever had on that type of submission along with a favorable outcome.
2. Use AI as a Startup Therapist
Tensions high? Morale low? AI can help you role-play the situation and even assess from your team’s perspective. I’ve even used it to mediate and help me set boundaries as well as talking through how I can make a hard decision without devastating my team. Empathy and perspective take emotional energy. Instead of taping reminders to breathe on your computer screen, now you can just vent into an AI assistant and probably get a more thoughtful and helpful (and HR approved) outcome.
When actions of one of your team members become problematic, you probably experience some anxiety about what to do about it. I know I do. I’m tempted to react in order to get the hard decision over with. Reaction isn’t usually super helpful. Instead, I used my AI therapist to discuss how my decisions to fire/hire impact my team and whether our mission may be damaged by the loss of their skillset.
In alternate, I also use it for positives. We had an executive coaching session with leadership recorded by Fireflies. I took those notes and used ChatGPT to create a rubric for myself to improve my leadership. THAT is what I have taped to my computer screen now.
Side Note: Don’t upload personal employee data. There are still laws about that.
3. Brainstorm Without Wearing Out Your Team
AI is the colleague who never gets tired of your “what if we…?” thought spirals. It will happily poke holes, spin alternatives, or suggest adjacent opportunities. You can’t emotionally exhaust it like you can your teammates.
I love ideas and projects. Whatever we can do to change the world for the better, faster. We all know that one teammate who lives in the future but never actually ships. AI can babysit them until they do! Give these people guardrails by telling them to create a fully baked project plan with AI before they present it to other humans. I created a project form for myself that forces me to think through hard questions my colleagues might have prior to me putting it on the calendar for discussion.
It’s me. I’m the problem, it’s me.
4. Craft Emails That Actually Land
We’ve all written that one email we thought was crystal clear but obviously still miscommunicated our message. I usually find this out after long bouts of silence or suspiciously passive aggressive responses over time. I rather just tone check myself from the start.
Literally, paste your draft and ask: “How will they hear this?” or “Do I sound like a jerk?” I’ve also shamelessly asked: “Do I sound like I know what I’m talking about?” Because let’s be real, imposter syndrome is alive and well in startup land.
If I’m being honest, I’ve also used AI tone checking for evil. I had this one contractor who was obviously in breach of contract and flaking on every, single deadline. “Make me sound more intimidating and use all the legal words.” What can I say– I’m in my villain era.
5. Organize the Data You Didn’t Know Was Data
AI doesn’t just crunch spreadsheets—it can help make sense of people. People are the hardest part of running a successful business. You MUST understand them just like your product and mission. We fed it leadership profiles (think Myers-Briggs) alongside our org chart, handbook, mission, and goals. It spit back workflows that amplified team strengths, reduced friction, and aligned growth goals with company objectives.
It helped us align growth goals with company objectives, divided leadership lanes, and even designed a bonus structure that matched our values.
If you’re not using AI for soft skills, you’re totally losing out on some value. Yes, most of the value is not quantifiable. There are no KPI’s directly aligned with my five suggestions. However, you also won’t lose anything for giving it a try.
Note: The AI sucked at writing this article.