Groping Around in the Dark

No shit, there I was, learning how to navigate with a compass and a map at night.

The forest was pitch black.

No GPS, no phone, just me, a paper map, a compass, and the vague idea that I was supposed to find a series of small barrels somewhere out THERE.

A lot of people are terrible at it…. Drifting off course and walking in circles.

I was taught a MUCH simpler way to navigate at night that routinely saved my bacon… catching features and handrails.

Those two silly ideas saved my ass, and I still use the concepts today in my business (and so should you)!

A catching feature is a big, obvious landmark that tells you you’ve gone too far—like a stream or a road.

You’d have to be an idiot to go past this, even when it’s pitch black… “Do not cross a river, or you are F’d”.

Somewhat similarly… a handrail is a feature you can follow to stay on track—like a trail, a ridge line, or a power line.

“Keep the mountains on your left, and don’t lose sight of them.”

The whole idea is that you don’t have to be too precise to stay on track.

You don’t need precision.

You just need a general plan and a few clear signals to tell you if you're going the right way—or way off.

It’s the same with delegation.

Most delegation in small businesses fails because we either:

• Overload people with step-by-step instructions (micro management)

• Toss the task over the fence with zero guidance (abdication)

Neither works.

The first disempowers your team.

The second screws up quality.

What works better is giving your team a compass, a map, a route to try—and then agreeing on the handrails and catching features.

CURE #1: DEFINE THE BOUNDARIES UP FRONT

In business, a handrail might sound like:

• “Use last month’s client proposal as a reference—same structure, same tone.”

• “Follow the current SOP unless the client asks for something clearly outside the lines.”

• “Stick to the pricing table in the Airtable sheet. That’s your boundary.”

These help someone stay on course without having to guess which direction they’re supposed to be going.

A catching feature might be:

• “If the client ghosts for more than five business days, flag it.”

• “If you’ve written three cold emails and still don’t feel good about any of them, pause and check with me.”

• “If this takes more than half a day, something’s off. Let’s regroup.”

It’s the equivalent of “If you cross the stream, you’ve gone too far.”

These kinds of cues are simple.

They let people operate independently but with guardrails.

They know when to move and when to stop.

You know when to trust and when to step back in.

It’s not a checklist.

It’s a mutual agreement on what success and failure look like, and how to course-correct before things blow up.

CURE #2: IF YOU WANT TO BE LESS INVOLVED, BE LESS SNEAKY (AND MORE CLEAR)

When delegation goes badly, it's usually because someone wandered off into the woods and didn’t realize it.

They didn’t know what “too far” looked like.

They didn’t have a handrail to follow…. And you didn’t give them one.

A few people might say, “Just let them figure it out.”

But that’s not trust—that’s abdication.

You can’t expect people to succeed if you haven’t even shown them the map.

When someone’s new, your handrails and catching features will be tighter and more frequent.

That’s fine.

Over time, you spread them out.

Give people more space.

But you always keep some in place.

“Don’t hire someone above XYZ rate without asking me”.

I've used this approach in hiring, in onboarding, in customer work, in ops.

When I remember to do it, it saves time, prevents rework, and makes people more confident in their decisions.

When I don’t, I end up frustrated and surprised—and that’s on me.

So next time you’re handing something off, don’t just say “keep me posted.” Say:

• “Stick to X until you hit Y.”

• “If Z happens, stop and let me know.”

It takes 30 seconds.

But it could save you hours—and a whole lot of backtracking

Yallah Habibi,

Jon

P.S.

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- Air Conditioning and Plumbing Company based in Texas

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- Construction Company Based in Arizona

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- B2B Podcast Agency

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