🪵 Your systems will win

A couple weeks ago, I decided I was going to lose 20 pounds in 10 weeks.

I was all in.

I had everything I needed:

A strong plan.
Meals mapped out.
Groceries.
Even ChatGPT helping me think it through.

Day one: 14,000 steps, great meals, felt locked in.
Day two: same thing.
Day three: still going.

I was on my way.

Then reality showed up.

I ran out of groceries.
I had a work breakfast I forgot about.
My son had a late-night theater thing… which ended with our McDonald’s tradition.

And just like that, I was off.

I’ve been thinking about that a lot.

Nothing was wrong with the plan—I knew what to do. I had the motivation. I had momentum.

But my life wasn’t set up to support it.

And that’s the part that sticks.

We like to think behavior change comes down to willpower, discipline, and having the right plan.

But most of the time, we’re just operating inside systems that don’t support the behavior we’re trying to change.

And the system wins.

✨ Why this matters

Leadership development runs into the same challenge.

We give leaders content, frameworks, training, coaching. All of it can be helpful.

But then we drop them right back into the same system:

The same packed calendars.
The same meeting overload.
The same expectations to move fast.
The same pressure to keep everyone happy.
The same incentives that reward output more than reflection.

And we hope something changes.

We ask them to have better conversations but don’t give them more space to prepare for them.

We ask them to coach more but keep them buried in reactive work.

We ask them to lead differently without changing much about the environment they’re leading inside.

That’s the part I keep coming back to.

Most leadership challenges aren’t just about what someone knows—they’re about what their system makes easy (and what it makes hard).

And if the system keeps rewarding speed, urgency, and short-term output, it’s not surprising when thoughtfulness, feedback, and presence are the first things to go.

🔥 Something to share

If you’re supporting managers right now, it might be worth shifting the question a bit.

Instead of: “What should they do differently?”
Try: “What in their environment makes this hard to do consistently?”

Because even small things matter…

- How much time they actually have between meetings.
- What gets rewarded (and what doesn’t).
- Where they feel pressure to move fast instead of slow down.

Those are the things that shape behavior.

🔦 What we’re hearing

When things don’t stick, it usually sounds like this:

“It worked in the session… just not in the week after.”
“They don’t have time to do it the way we talked about.”
“It feels right in theory, but hard in reality.”

There’s usually not a lack of understanding.

People get it. They can explain it back. They agree with it.

But when the week picks up, meetings stack, priorities shift, things move faster than expected—and the old patterns take over again.

Final thought:

In trying to lose 20 pounds, I didn’t fall off track because I didn’t know what to do.

I fell off because my life wasn’t set up to support it.

The only plans that work are the ones your life can actually hold—the ones that still work when things get busy, plans change, and real life shows up.

Same thing with leadership.

If the system doesn’t support the behavior, it won’t show up consistently. No matter how good the training is.

I’m still figuring this out myself, but I’m thinking a lot more about these questions:

What makes this easier to repeat?
What gets in the way?

I’d love to hear what you’re seeing in your own organization.

Warmly,
Steve

Sent from Campfire—a hub for developing leaders at scale.