Everyday Run State: Pro Edition

I make small changes in my personal life. Tiny ones. I’ll tweak a morning routine, test a new workout, or slowly phase in a new supplement to see how it feels.

But professionally? I love big, structural change.

The kind that reshapes how teams operate, improves flow, and gets measurable results.
I am finding I am very much in the minority here - even though everyone says they want change, and that the are ready for change, when push comes to shove, there’s going to be friction against challenging the status quo.

When I’m helping a client implement something new, the first step isn’t the project plan - it’s taking the company’s temperature for change. Because every business has its own personality, and change management that works brilliantly in one organization can completely flop in another.

The most obvious sign that a company isn’t ready? When a leader asks for best practices… and then instantly shuts them down.

If the response to a new idea is a hard “No, that won’t work for us” - without reasons, context, or even a “not yet, and here’s why” - it’s not a process problem. It’s cultural. Something in the leadership or team mindset isn’t ready to explore change. And until that shifts, even the best tools and systems won’t stick.

Culture as Personality

This is where I think about Gretchen Rubin’s Four Tendencies - it’s a simple framework for how people respond to expectations and change:

• Upholders – love structure, rules, and clear expectations.

• Obligers – need external accountability and client-driven motivation.

• Questioners – want to know why before committing to something new.

• Rebels – resist structure and thrive on autonomy and innovation.

Now, imagine that as an organizational personality:

• An Upholder company loves SOPs, dashboards, and compliance. They’ll adopt a new process quickly if it’s well-defined.

• An Obliger company jumps through hoops for clients but struggles with internal change because it doesn’t feel “urgent.”

• A Questioner company needs to see the data before acting - show them the ROI and they’re all in.

• A Rebel company hates rules but excels when you frame change as freedom or innovation.

This is incredibly frustrating if you, personally, have a different personality than your company culture. However, if we all had the same tendencies, the world would be an incredibly boring place.

As an Upholder myself, I need Obligers to remind me of the value of community and accountability, Questioners to slow me down and remind me to look at a problem from multiple angles, and Rebels to force me to think outside the box and be creative.

I’ve created a matrix below which has helped me when working with my clients - find your tendency in the first column, and then read across the row for your company’s tendency.

In the Portal - The WiseOps Collective

If you missed it, my Membership Library has a new name: The WiseOps Collective.

This is my digital, AI-searchable library for ConnectWise PSA users - filled with walkthroughs, SOP templates, and best practices for managing Procurement, Projects, and more. You can even post questions in the discussion portal, and I’ll record custom video walkthroughs for you.

Recent uploads include:

• Procurement Setup Refresher

• Project Billing Workflow SOP

• Top ConnectWise Shortcuts & Hidden Tools

👉 Join or Log In to the WiseOps Collective

Final Thought

Change doesn’t fail because of bad planning - it fails because it doesn’t fit the personality of the people implementing it.

So before your next big shift, ask yourself: what kind of company are we?
Because a great process only works if your culture is ready to follow it.