
Some people start with the problem. Far starts with the truth underneath it.
As my cofounder and the person responsible for design and direction across everything we build, he thinks in first principles — tracing every problem back to its root before he touches the detail.
We don't subscribe to traditional titles at Out of Office – so his is Head of Tea.
This week, he's writing The Huddle.
Most problems aren’t in the details, they are in the perspective.
My co-founder looked at me from across the table and said, "I don't understand why the fuck I have to explain this three times."
She wasn't asking. She was done.
Someone on the team had missed the mark again — not because they lacked the instructions, yet because they fundamentally didn't see what "good" looked like.
She'd documented it. Walked them through it. Recorded a Loom.
And still: crickets where clarity should've been.
I recognized the exhaustion in her voice because I'd felt it a hundred times before.
That specific flavor of frustration — when you realize the problem isn't the process.
It's that you're building into concrete while assuming everyone else sees wood.
Here's what I've learned the hard way: misalignment doesn't announce itself in the big moments.
It shows up in the small ones.
The Slack message that takes four rounds to land. The deliverable that's technically complete yet fundamentally wrong. The meeting where everyone nods and nothing changes.
You start thinking the person doesn't care. Or isn't capable.
Most of the time, they just don't share your definition of "done."
Same inputs. Different orientation.
I've walked plenty of people through a 25-step process and watched it fail — not because the steps were wrong, yet because we never agreed on what we were building toward.
I was optimizing for speed. They were optimizing for safety.
Neither of us was wrong. We were just pointed in different directions, hammering away, wondering why the other person wasn't keeping up.
When orientation isn't aligned, everything becomes friction.
You start resenting the person you're supposed to be coaching. You over-document to compensate for their lack of judgment. You tighten control and call it quality.
The team becomes dependent because nobody actually owns the why.
And then you wonder why leadership feels so damn heavy.
Most leaders fixate on the micro — the missed step, the imperfect wording, the process that needs one more iteration.
But if two people walk into the same project with entirely different pictures of success, the details are a distraction.
You're arguing about the vehicle while you haven't even agreed on the destination.
Zooming out doesn't remove the difficulty.
It just changes what the difficulty means — whether it feels like progress or punishment.
Before you rewrite the SOP, before you add another checkpoint, before you get consumed by why this person "just doesn't get it" — ask yourself if you've actually aligned on what good looks like.
Not in theory. In practice.
Because if you keep arguing about the process, you're avoiding the harder conversation.
You don't agree on what matters.
You'll be seeing more of him over the coming months, so if how he thinks resonates with you, go give him a follow.
Appreciate you being here in the Huddle. For deeper dives into leadership and culture, join us at Out of Office: The Experience on YouTube and Podcast.
– The Huddle
P.S. Know a leader who’d value this? Forward them this week’s Huddle.

