Do You Think About Rethinking?

Author: Felice Upton | Connect on LinkedIn
Published January 6, 2026

Do You Think About Rethinking?

Here's a question I rarely hear in meetings, but when I do, it's cause to get excited:

"Does this data actually mean what we think it means, or did we just quiet one problem and create another somewhere else?"

It's not that leaders don't care about good decisions. It's that most organizational cultures aren't built for rethinking. They're built for deciding, moving, and defending.

But in human services and justice systems, where our decisions affect safety, liberty, and people's futures, the ability to revisit, question, and revise isn't a luxury. It's a responsibility.

The Rethinking Gap

After years identifying systemic issues that allowed terrible things to happen, and now consulting with organizations to solve them, one pattern shows up everywhere:

We celebrate decisiveness. We rarely celebrate revision.

Think about your last few leadership meetings. How often did someone ask:

• "What if we're wrong about this?"

• "What would need to be true for us to change course?"

• "Are we solving the problem, or just moving it?"

• "Will this decision cause new issues?"

If those questions feel risky to ask in your organization, that's information. It tells you something about your culture, not your people.

Confirmation Bias Doesn't Announce Itself

I think and talk a lot about confirmation bias, our tendency to seek information that supports what we already believe and dismiss what complicates it. If we've ever worked together, you know this.

Here's the thing: you can't think your way out of confirmation bias alone. You need a culture that makes it safe to surface disconfirming information. You need people who are willing to say, "I'm not sure this means what we think it means," and be heard, not sidelined.

Without that, even well-meaning teams end up:

• Recycling the same initiatives under new names

• Defending metrics that look good but don't reflect reality

• Labeling people as problems instead of questioning the system

• Not understanding the actual cause of the issue and fixing what we assume caused it

• Promoting the people who tell leadership what it wants to hear

• Watching the truth-tellers leave while the cover-up artists climb

What a Rethinking Culture Actually Looks Like

Let me be clear: rethinking is not indecision. It's not second-guessing every move or getting stuck in analysis paralysis. It's building in moments, and permission, to pause. To ask whether the path you're on is still the right one. Most organizations confuse speed with progress. A rethinking culture knows the difference.

A few practices I use with leaders:

Separate the data from the story. Data doesn't speak for itself. It speaks through whoever is holding the mic. And the meaning we assign to it says as much about us as it does about what happened. Before interpreting results, slow down and ask: What do we actually know? What are we assuming? What are we believing but haven't tested? The answers might be uncomfortable. That's usually a sign you're asking the right questions.

Assign a constructive challenger. Not a devil's advocate for the sake of argument, but someone whose job is to ask what's missing. And here's the part most teams get wrong: that person needs to be neutral. Not someone with a stake in the outcome. Not someone who benefits from being right. If your challenger has skin in the game, they're not challenging. They're lobbying.

Revisit decisions as conditions change. A good decision six months ago might not be the right decision now. Conditions shift. New information emerges. People leave. Build in reflection loops, not just implementation timelines. And ask the question most teams skip: what are the multiple paths to completion? If you only see one way forward, you're not planning. You're hoping.

Watch your own reactions. When someone raises a concern, do you get curious or defensive? Your response teaches people what's safe to say. And if your team never pushes back, it's worth asking why. Maybe they've given up trying. Maybe they're waiting for you to fail. Or maybe, and I say this with love, you're not running a team. You're running a cult.

The Loneliest Work in Leadership

The leaders I trust most aren't the ones who are always certain. They're the ones who stay curious, stay grounded, and stay willing to revise. They create space for hard questions and resist the pressure to perform confidence they don't feel.

But here's what I've learned: those leaders need support too. Rethinking is lonely work when your culture rewards certainty. It's hard to question your own assumptions when everyone around you is invested in the current answer. Sometimes the most valuable perspective comes from outside your system, someone who can see what proximity makes invisible and ask the questions your team has stopped asking.

In systems designed around control, rethinking feels risky.

In systems serving human beings, it's essential.

So, I'll ask you directly:

Does your culture make it safe to rethink? Or does it only reward being right the first time? Is it okay to have been right then and be wrong now because conditions changed? Or does your organization treat changed minds like character flaws?

If you're now rethinking whether your organization actually makes space for rethinking, congratulations. It's working.

If you're rethinking rethinking and want someone to rethink with, reach out. I promise not to say "I told you so" when you change your mind.

Because you will. That's kind of the point.