Choice over Comfort: the curse of autopilot

I know these roads so well, I know exactly where to turn…
And therein lies the problem.

Last week, I was driving to the Yarra Valley for an offsite. Because we’d recently moved house, the route was a new one for me.

At least, that’s what I thought.

The first part of the drive felt oddly familiar. It turns out this new route shared a lot of the same roads and freeways that I’ve driven a hundred times before—just usually to very different destinations.

That’s when things got interesting, as I found myself cycling between two states of mind:

“Where does Google want me to turn next?” (unknowing)

“Oh, I know this road… I know exactly where to turn!” (expert)

The problem was, once I slipped into expert mode, I stopped paying attention to what I didn’t know.

Distracted by the conversation with my passenger, I kept missing Google's turn-offs!

Ah, autopilot.

We assume we know the way—so we stop looking for new routes.

We follow familiar roads—so we miss the smaller paths that might take us somewhere better.

Autopilot is our Frenemy

Autopilot isn’t about being complacent—it’s about relying on your ability to predict what should happen next.

But once we assume we know the way, we stop seeing the smaller paths that need to be taken—or that could be explored.

This shows up in:

• Facilitating conversations: Defaulting to the same voices or presenting content because it’s easier than opening up space.

• Advising clients: Offering familiar solutions instead of challenging the status quo.

• Making decisions: Choosing what feels safe instead of exploring the ‘what ifs’.

Our expertise traps us in predictable paths—and that’s when we miss the opportunity to make a real difference.

 Choice Beats Comfort

 The best leaders aren’t the ones who know the roads—they’re the ones who question the route.

It’s about choosing curiosity over certainty.

Here are 3 simple ways to do that:

Pause to question familiar paths:

Ask: “If we couldn’t take the usual path, what’s the alternative?”

Or: “If we invited [X] into the room, what would they say we’ve missed?”

Shine a light on assumptions:

Ask: “What’s one thing we’re assuming that might not be true?”

Or: “What are we assuming are the criteria for making the best decision here?”

Invite fresh voices:

Ask: “Who haven’t we heard from yet—and what might they see differently?”

Or: Reserve an extra seat in important meetings for a ‘special guest perspective' (ideally a contrary view)

Autopilot is a choice too

Being choiceful isn’t about rejecting your expertise—it’s about deciding when to trust it and when to switch it off.

The goal isn’t to never use autopilot; it’s to know when to override it.

So, over to you: What’s one familiar path you could step off and question right now?

Until next time,
Simon