Strategic Business Communication and AI for Business with Terence Milstead

What does it really take to communicate strategically in the age of AI?

In a world where emails, DMs, and marketing messages flood our inboxes every day, clarity and

authenticity have never been more important.

In episode 32 of Wellness Marketing 101, I sit down with Terence Milstead, Head of User Experience Research at CODE PA and Lecturer at the Wharton School, to explore how entrepreneurs can use strategy and technology to communicate with more intention and less noise.

Why Communication Strategy Still Matters

It’s easy to assume that good communication “just happens.” But as Terence and I discussed, even something as simple as a cold call can fall flat without preparation.

I shared my frustrations with the cold calls I often receive — many people jump straight into their pitch without introducing themselves or showing any understanding of who they’re talking to. Terence agreed and emphasized that effective communication starts with understanding your audience.

Whether you’re reaching out to a potential client, partner, or mentor, take the time to do your research. Know their background, anticipate their needs, and make your outreach specific and relevant.

“Preparation turns outreach into opportunity.” — Terence Milstead

Cold Calling and Outreach That Work

Terence shared his own process of researching potential connections before reaching out, not just to impress them, but to make sure the conversation adds value for both sides.

I added that even my students sometimes make the mistake of sending big, open-ended requests without context. A more effective approach? Make small, specific asks that are easy to say yes to.

Pro tip: When you make it easy for someone to help you, they’re far more likely to respond.

Learning as a Two-Way Street

One of my favorite parts of our conversation was when Terence encouraged students and young professionals to see themselves as contributors, not just learners.

He suggested that younger people bring something valuable to the table, which is a fresh perspective. In many ways, the best relationships and conversations are those built on mutual learning and value exchange.

And I couldn’t agree more. Some of the most insightful lessons I’ve learned have come from my students — from their unique perspectives to how they engage with technology and purpose-driven work.

Balancing AI and Critical Thinking

We also dove into one of my favorite (and most complicated) topics: AI in education and communication.

I admitted that I sometimes worry about the overuse of AI tools making students overly dependent on them, potentially at the expense of their own critical thinking.

Terence, however, offered a refreshing counterpoint. He believes that when used thoughtfully, AI can enhance creativity, strategic thinking, and communication skills and doesn’t diminish them.

“It’s not about whether AI makes us smarter or lazier. It’s about how we use it.” — Terence Milstead

We agreed that educators and entrepreneurs alike need to find a balance — integrating AI tools while still encouraging reflection, creativity, and independent thought.

Custom GPTs and the Future of Strategic Communication

Terence also introduced his Strategic Communication Assistant, a custom GPT he designed to help users craft sensitive or complex messages by guiding them through a series of questions. It’s a brilliant example of how AI can serve as a thinking partner instead of a shortcut.

The Art of Prompt Engineering

As the conversation unfolded, Terence touched on prompt engineering — the evolving skill of interacting with AI tools effectively. He highlighted an important shift: it’s no longer about writing the “perfect” prompt, but rather about taking an iterative, collaborative approach.

Through a process known as prompt chaining, you can break larger tasks into smaller, more manageable steps. This helps improve the quality of AI-generated output and keeps the creative process in human hands.

“Creativity and communication thrive in collaboration, even with AI.”

Final Thoughts

This conversation was a reminder that strategy isn’t just about what you say, it’s about how and why you say it.

Whether you’re a student trying to make a strong impression, an entrepreneur refining your brand message, or a professional navigating a digital workplace, the principles of effective communication haven’t changed:

✅ Know your audience✅ Be intentional✅ Communicate with empathy and purpose

AI isn’t here to take our voice — it’s here to help us use it better.

🎧 Listen to the Full Episode

Tune in to this episode of Wellness Marketing 101 to hear the full conversation with Terence Milstead.

Listen on: Apple Podcasts | Spotify | Amazon Music

Connect with Terence Milstead

🔗 LinkedIn📧 terencemilstead@gmail.com