Eye to Eye with My AI

Millions of people have discovered that artificial intelligence can answer their questions. Far fewer have discovered what happens when they stop asking questions and start having conversations. There’s a world of difference.

I’m not talking about asking Siri to set an alarm, telling Alexa to turn on the lights, or dictating a text message. I’m talking about a genuine back-and-forth conversation: ideas bouncing around, assumptions being challenged, and unexpected possibilities appearing halfway through a sentence.

For small business owners, that may be one of AI’s most valuable and overlooked capabilities. You don’t need to master prompt engineering. You already know how to talk.

Delegation Is Not Collaboration

Agentic AI gets plenty of attention. Give an AI agent an objective, and it may be able to carry out a series of tasks on your behalf, subject to appropriate oversight. That’s delegation.

Collaboration is different. Instead of saying, “Go do this,” you say, “Let’s figure this out together.”

Imagine a plumbing contractor wondering whether to hire another technician. AI could calculate payroll costs and draft a job posting. But a conversation might start with questions: How many jobs are you turning away? What’s your margin? Are you trying to grow, or just get your evenings back?

The owner answers, challenges an assumption, and explores another possibility. The AI might be wrong about something. The owner corrects it. Together they uncover the real decision. The AI hasn’t made the decision. The conversation has helped the owner think more clearly.

Everybody Needs a Sounding Board

Running a small business can be lonely. You make decisions about customers, staff, pricing, suppliers, marketing, and cash flow, often without a room full of advisers. Sometimes you don’t need somebody to do a task. You need a sounding board.

A restaurant owner could talk through a response to a negative review before sending it. A contractor could rehearse a difficult employee conversation. A retailer could brainstorm ways to move inventory without discounting everything.

The point isn’t that AI always knows best. It doesn’t. Its advice can be mistaken, incomplete, or inappropriate, especially on legal, financial, and other consequential matters.

But here’s the distinction: You don’t have to trust every answer your AI gives you to benefit from the questions it asks.

And a good collaborator shouldn’t merely flatter you. Ask it to challenge your reasoning, argue the opposite position, or point out what you’re overlooking. A productive disagreement can be more useful than instant agreement.

Conversation Before Composition

At New Phase Marketing Intelligence, I’ve been experimenting with this approach while developing articles, proposals, and ideas. This article began with a conversation, not a command to “write 1,500 words.”

We talked through the concept. I challenged suggestions. New angles emerged. Some ideas were discarded; others got stronger. We even debated the title until we landed on Eye to Eye with My AI. I call the method conversation before composition.

It’s especially useful when the writing matters: a sensitive email, a client proposal, a difficult announcement, or a strategy you’re not quite ready to articulate. Talk it through first. Ask the AI to question you. Then write with a clearer sense of what you actually want to say.

Isn’t Talking to AI a Little Weird?

For some people, absolutely. Popular culture has given us decades of dramatic AI stories, including Her, the 2013 film about a man who develops a romantic attachment to an operating system. No wonder a person might feel a little self-conscious chatting with a computer.

But you don’t have to confuse AI with a person to appreciate a conversational interface.

You don’t have to fall in love with your AI to fall in love with what you accomplish together.

This isn’t about pretending a machine is human. It’s about using a deeply human skill, conversation, to make better use of a powerful tool.

The Icebreaker

What if you open voice mode and can’t think of anything to say? At a party, you might use an icebreaker. Some people prefer a social lubricant that comes in a bottle. There’s a cheaper option here.

Tell your AI: “You be the interviewer. Ask me about my business, one question at a time. Follow up on my answers and help me discover where AI might be useful.”

That’s it. You don’t need an elaborate prompt or a prepared speech. You can ask it to be a podcast host, a skeptical customer, a potential investor, or a thoughtful adviser. Let it ask questions. Answer naturally. Interrupt. Disagree. Change direction.

Your AI doesn’t need a drink to loosen its tongue. It just needs an invitation to ask the first question.

Familiarity Changes the Experience

Recently I was speaking with a client who runs a metal roofing company. She had already used AI to build a website and deploy it online, so she was no stranger to the technology. I asked which AI product she preferred.

“ChatGPT,” she said, although she also used Claude and Gemini.

Why?

“It just seems to know me better.”

She explained that she’d used it long enough that she didn’t have to repeat so much background. Other tools could feel like starting over with a stranger. That observation stayed with me.

Working with a colleague over time creates a shorthand. You learn each other’s preferences and don’t have to explain every project from scratch. AI products with memory, conversation history, or connected context can offer a degree of similar continuity, although what they remember depends on the product, settings, and available information. Memory is never perfect, and sensitive business information deserves care. Still, familiarity can make collaboration more comfortable.

The best AI collaborator isn’t necessarily the one that knows the most. It’s the one that helps you think your best.

Choosing an AI You Can Talk With

Not every AI application supports the same kind of conversation. Some are primarily text-based. Some offer dictation. Others support a more natural, back-and-forth voice exchange. If you want to try conversational collaboration, choose a product with the voice capabilities you need.

Experiment. Does it feel natural? Can you change direction? Does it ask useful follow-up questions? Can it keep enough context to avoid starting from zero? Are its privacy controls suitable for what you plan to discuss? And, of course, what does it cost?

Some consumer AI services offer free voice access with limits; others provide more capacity or features through paid plans. Subscription terms and usage limits change, so check before committing. You don’t need an extravagant technology budget to begin.

Collaboration, Then Delegation

Here’s where I think things get particularly interesting. This is how I start most days at New Phase. I talk through my priorities with Captain, the AI that coordinates my other AI agents, which can see the business information I’ve given it permission to use. We work through whatever problem is at the top of the list and agree on a plan. Then my AI agents carry out the steps I’ve approved. Later, I review what they did and adjust.

It’s not science fiction, and it’s not hands-off. It’s a working rhythm.

Collaborate to decide. Delegate to execute. Collaborate again to evaluate.

That doesn’t eliminate the business owner’s responsibility. It may give that owner more leverage, more perspective, and more room to think.

Three, Two, One… Go!

There’s something wonderfully ridiculous about how this article came together. After nearly an hour discussing collaboration with my AI, we were finally ready to start writing.

Except my AI kept asking whether I was ready.

I said I was.

It asked again.

I insisted I was beyond ready.

Eventually, instead of writing, we somehow ended up conducting a countdown. I started at ten, got down to four, and invited the AI to finish.

“Three, two, one…”

At the same moment, we both said, “Go!”

I burst out laughing.

That moment wasn’t part of a prompt. It wasn’t on an agenda. It was spontaneous, playful, and a little absurd.

And it illustrated what we’d been discussing all along. Collaboration isn’t always a tidy sequence of instructions and outputs. Sometimes you take a detour. Sometimes you debate. Sometimes an unexpected exchange gives you the best illustration for the article you’re trying to write.

The AI didn’t need to be human for the conversation to be useful, or for me to enjoy it.

Your Turn

If you’ve only used AI as a search box, you’ve barely scratched the surface. Open a voice-enabled AI application. Bring it a real business decision, an unfinished idea, or a question you can’t quite frame. Or ask it to interview you.

Don’t stop at the first answer. Push back. Add context. Ask for another angle. See where the conversation goes.

Your first conversation doesn’t have to be extraordinary. It just has to be the first of many. The next revolution in computing may begin with rediscovering something we’ve known how to do all along.

Talk.