Software is easy. Humans are the hard part.

What companies get wrong about digital transformation—and what to focus on instead.

Author

Reade Milner
June 10, 2025

This 3-minute read brought to you by the team at Rogue Pine

In this issue, you'll learn:

Most digital transformation efforts fail before they begin.

Not because the tech is wrong. Because the people aren’t ready.

In this episode of the Grow Rogue Podcast, I sat down with Tom Brouillette—a 40-year veteran of digital change, supply chains, and systems thinking.

We talk about what’s actually required to evolve how we work.

Tom’s been through it all. Legacy ERP rollouts. AI initiatives. Full-scale digital shifts.

His perspective is simple: software isn’t the hard part. Getting humans to think and operate differently is.

Here’s what we took away from the conversation—and what to do if you’re navigating something similar.

1. AI is changing how we work—but not the challenge

Tom said it clearly: AI tools give us faster thinking, better context, and stronger focus.

The capabilities are real.

But adoption is still slow. Not because the tools are lacking—but because most teams aren’t ready to operate differently.

The bottleneck isn’t tech. It’s mindset.

What to do if you're here: If you're investing in new tools or platforms, start with your people.

Ask how they’ll use it, what they’re concerned about, and how it supports their actual goals. If those answers aren’t clear—pause the rollout.

2. Digital success is about storytelling, not just data

I asked Tom how leaders can get teams to embrace change. His answer? Make them care.

The information is already out there. What’s missing is the story that helps people connect the dots.

AI can gather and organize knowledge. But the message still has to land.

What to do if you're here: If you're communicating strategy, don’t lead with numbers.

Lead with clarity. If your message isn’t sticking—internally or externally—that’s often where we come in.

We help teams build content systems that actually connect.

3. Supply chains are broken because they were built for cost—not resilience

Tom talked about this a lot. COVID didn’t break the system. It exposed it.

Most supply chains were designed to be efficient, not adaptive. When one piece fails, everything freezes.

That’s why Tom says we don’t need supply chains—we need supply networks. Systems that are dynamic, observable, and collaborative.

What to do if you're here: If your operations rely on external systems or partners, look closely at how connected your infrastructure actually is.

Can your team adapt quickly? Can you spot friction early?

If not, the issue may be structure, not speed.

4. If you want adoption, start with value

“Software doesn’t change the world. People do.” That was one of Tom’s core points—and it stuck.

Most teams resist change when they don’t see how it helps them win.

People need to know:

  • How does this help me today?

  • What’s in it for my team?

  • Will this make my job easier or harder?

What to do if you're here: Whether you're rolling out a CRM, newsletter, or internal playbook—make the benefit specific and personal. We often help teams bridge that gap, especially when content adoption or sales alignment is missing.

Final thought: Tools are multiplying. Strategy still matters.

AI is making a lot of things easier. But it won’t make your team care.

That’s still your job as a leader: to clarify the plan, shape the message, and build the trust it takes to move.

If you're leading through change, this episode is worth your time.

Listen to the full conversation with Tom Brouillette.

Is your content keeping up with your growth?

We work with founder-led teams and growing companies to simplify the way they communicate—with clients and their own team. If you’re navigating change, rolling out something new, or just tired of inconsistent content, here’s how we help:

→ Newsletter Strategy & Execution
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If you're growing—but the content hasn't caught up—we can help you get clear and move faster.