Working with AI did not make me more aggressive. It made me clearer. That shift changed how I negotiate, how I price, how I communicate, and how I protect my time.

The Habit I Didn’t Realize I Had

For most of my adult life, I have been a people pleaser. I acknowledge it, and even self-deprecatingly joke about it often.

It sounds harmless. Even noble. But in business, it quietly shaped how I negotiated, how I sold, and how I positioned value.

In conversations, I would start halfway.

Before the other person even reacted, I had already adjusted. I would think: How do I make this easier for them? How do I remove friction? How do I solve their problem first?

On the surface, that looks collaborative.

In reality, it often meant I was negotiating against myself.

I would frame sponsorships as if someone were doing the Chamber a favor. I would present pricing cautiously, almost apologetically. I would enter entrepreneurial conversations assuming I needed to justify my worth before it had even been questioned.

The unintended result was predictable: I would begin in the middle and end up further on the other person’s side in the name of “mutual benefit.”

No one asked me to do that. I just did.

What Changed (And Why I Didn’t Expect It)

What changed recently is something I didn’t expect.

Working with AI, particularly using ChatGPT to think through positioning, pricing, proposals, and even difficult conversations, has fundamentally changed how I approach these situations.

Not because AI made me more aggressive.

Because it made me clearer.

When you run your thinking through a system trained on best practices in negotiation, persuasion psychology, behavioral economics, and communication strategy, something interesting happens. It doesn’t get emotional. It doesn’t rush to please. It doesn’t avoid discomfort.

It reflects structure.

It forces you to articulate value plainly.

It highlights when you are pre-discounting.

It exposes when you are solving someone else’s internal decision-making process before they have asked you to.

Sales, Value, and Stopping the Apology

In Chamber sponsorship conversations, this shift has been noticeable. Instead of approaching a $1,500 sponsorship as if I’m asking for help, I now frame it for what it actually is: a high-visibility, strategically positioned marketing opportunity we’ve worked very hard to build. There’s significant value in that.

If it aligns with your goals, let’s partner.

If it doesn’t, that’s okay too.

The tone is different. The posture is different. And interestingly, the outcomes are better, not just for me, but for the sponsors as well. Because the relationship begins with mutual value, not self-discounting.

The same has happened with Momentum AI. As entrepreneurs, we all talk about undervaluing ourselves. It’s almost a rite of passage. But clarity changes that dynamic. When pricing reflects delivered value instead of insecurity, the conversation becomes healthier.

I know that our AI work for companies can save thousands, if not tens of thousands, of dollars, yet I still approached sales conversations hat-in-hand.

As soon as I let down my own guard, and started quoting things based on the value that would be provided, not what I think they would pay, we’ve started picking up contract after contract.

AI didn’t change my personality.

It stopped me from negotiating against myself.

A Third Example: Boundaries in Everyday Relationships

There’s a third example that has nothing to do with sales.

It’s interpersonal.

When you’re a people pleaser, people get comfortable asking you for things. Your time. Your input. Your energy. Your problem-solving.

For years, in the name of relationship-building, I would accommodate. Even when someone was essentially taking work off of themselves and placing it onto me. Even when the project had very little to do with me in the first place.

I told myself I was being helpful. Collaborative. A good partner.

In reality, I was volunteering for responsibilities that weren’t mine.

Too many initiatives went nowhere. Too many hours were spent advancing ideas that someone else hadn’t even invested their own 50% into. And more often than I care to admit, I was left holding effort that never should have been mine, while my own projects and aspirations sat waiting for me to get to them.

Those who care about me, and who have invested in my success over the years, could probably point to a number of specific examples of this.

ChatGPT has been surprisingly firm with me here.

When I describe a situation and say, “They’re asking me to jump in on this,” the pattern recognition is immediate: Are they bringing their half? Is this aligned with your priorities? Is this a request or a transfer of responsibility?

It has encouraged me to be more respectful of my own time.

At minimum, someone needs to bring their 50% before I even get involved.

That shift has been huge.

Not colder. Not less generous. Just clearer about where responsibility begins and ends.

Decoding People Instead of Reacting to Them

But there is a second layer to this.

People are going to people.

Anyone who works in Chambers, associations, boards, or entrepreneurial ecosystems knows this. There will always be the skeptic. The chronic negotiator. The board member who derails meetings. The sponsor who wants premium exposure at bronze pricing. The member who pushes back reflexively.

Before, my options felt limited. Roll my eyes. Overcompensate. Avoid conflict. Give in. Go around. Find another way.

Now, I do something different.

I step away and think through it with AI.

“This person behaves like X. What might be motivating that?” “What incentive structure are they responding to?” “What language would resonate?” “How do I align this without surrendering value?”

That isn’t manipulation.

It’s strategy.

It’s the difference between reacting emotionally and responding intentionally.

The Subtle Pushback That Changed Everything

AI has become a kind of cognitive mirror. It gives me a structured place to test assumptions, to pressure-test tone, to remove ego from the equation before I walk back into the room.

There’s another subtle moment that has mattered more than I expected. Sometimes I’ll draft an outreach email or a reply, and ChatGPT will come back more direct, more forceful, than I would naturally be. My instinct is often to soften it. To round the edges. To make it more comfortable.

And when I push back, the response is often some version of: this is clear, this is fair, this is appropriate.

That gentle resistance, that “no, this is how you should do it” grounded in best practices rather than ego or wanting to just get along, has been a big lift for me.

More often than not, when I send the clearer, firmer version, the real-world results have been incredible. Faster decisions. Cleaner yes-or-no responses. More respect in the exchange. Not because I became harsher, but because I stopped cushioning the message before it even landed.

AI as Cognitive Regulation

And the irony is not lost on me. The tool that lives on a laptop screen has definitively improved my real-world interactions.

Clearer communication. Calmer posture. Stronger boundaries. Better partnerships.

We often talk about AI in terms of automation and efficiency. But one of its most underrated benefits may be cognitive regulation. A space to think clearly before you respond. A system that quietly references the accumulated best practices of business and human behavior.

It doesn’t replace relationships.

It sharpens them.

For me, that has meant better outcomes, not because I became harder, but because I became more aligned with mutual value.

And that shift has changed more than negotiations.

It has changed how I show up.