Kermit holding a coffee cup discusses software fixes; a dog in glasses humorously addresses management about project timelines.

The struggle is real.

Cloud didn't eliminate operational problems.

It just changed where they live.

You trade hardware issues for configuration issues. You trade capacity planning for cost management.

The work doesn't go away. It just evolves.

There are two types of documentation in IT:

📝 Documentation that doesn’t exist
📝 Documentation that exists but is no longer accurate

When your value comes from knowing every detail…
What happens when the platform starts managing itself?

Read Chapter 5 here: open.substack.com/pub/peoples...

Up to now, the team has been building momentum with automation, IaC, and observability.

Now comes the real challenge: letting go of control.

Chapter 5 opens with a DBA pushing back on managed databases.
And honestly, it's a fair reaction.

One of the best things a leader can say is:

“I don’t know, what do you think?”

Not as a deflection, but as an invitation.

You'd be surprised how often your team already has the answer.

And that's not a software problem. That's a business problem.

Because whatever you replace it with still has to handle admissions, enrollment, financial aid, student records, integrations, reporting, and about 20 years of institutional logic layered on top.

That's not just a system.

That's how the university actually runs.

Every time I hear “we just need to replace Campus Solutions,” I always pause for a second…

Replace it with what, exactly?

It is about creating a model for continuous improvement.

If you are a CIO or IT leader thinking about ERP strategy in 2026, this is the conversation to get right.

Read it here: open.substack.com/pub/peoples...

In this article, I lay out a step-by-step framework for building an ERP modernization roadmap that aligns with business priorities, reduces risk, and delivers measurable progress. This is not about a single transformation event.

Not because of poor execution, but because they start with a decision instead of a strategy. Too often, organizations jump straight to platform selection or migration timelines without fully understanding their current state or defining what success actually looks like.

Most ERP roadmaps fail before they ever begin.

Most outages don’t come from big, dramatic failures.

They come from small, reasonable changes that seemed like a good idea at the time.

That’s why discipline in change management matters way more than heroics after something breaks.

Leadership is usually the second one.

There’s a difference between being busy and being effective.

I’ve had days where I was slammed for 10 hours straight and accomplished almost nothing that mattered.

And I’ve had days where I made one or two key decisions that moved everything forward.

It’s building people who can succeed without you.

Servant leadership isn't about being passive.

It's about being intentional with where you spend your energy.

Sometimes that means stepping in to help.
Sometimes it means stepping back so someone else can grow.

The goal isn’t control.

I'm becoming a bigger fan of small, consistent improvements over big transformations. AI is reinforcing this.

The big stuff looks great in slides.

The small stuff is what actually changes how teams work day to day.

Every time we modernize something, we uncover five decisions from 10+ years ago that actually made sense at the time.

It's a good reminder: today's “why would they do that?" is tomorrow's “oh… now I get it."

PeopleSoft isn’t "old”, it's just very honest. 😀

It shows you exactly how your business actually works… not how you wish it worked.

That's uncomfortable sometimes, but also really useful if you lean into it.

One underrated skill: explaining technical things in a way that doesn’t make people feel dumb.

It’s harder than it sounds.

But it’s probably more valuable than knowing the technical thing in the first place.

I used to think confidence came from knowing the answer.

Now I think it comes from being okay not knowing, and still moving forward anyway.

That shift changes everything.

We spend a lot of time talking about modernizing PeopleSoft.

Less time talking about modernizing how we operate PeopleSoft.

The second one probably matters more.

The longer I work in IT, the more I realize leadership is mostly about removing friction.

Not adding process.
Not adding oversight.

Just quietly making it easier for good people to do good work.

Every time someone says "PeopleSoft can't do that," I get a little skeptical.

Most of the time, it's not that it can't… It’s that we haven’t figured out the clean way to do it yet.

There’s a big difference.

There’s a difference between being busy and being useful.

I’ve had days packed with meetings where nothing actually moved forward.

And then random 30-minute blocks where something real got solved.

Trying to chase more of the second.

I’m starting to think a lot of “complexity” in IT is just layers we never bothered to question.

Not all of it. But a surprising amount.

Sometimes the best move isn’t optimizing… It’s asking why it exists at all.

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PeopleSoft powers payroll, finance, and HR for thousands of organizations. How we deploy, automate, and modernize it needs to evolve.

I write about:
✅ Cloud-native deployments (any platform)
✅ Automation and platform engineering
✅ Leadership for ERP teams