The Issue I Guarantee You Have

Most founders treat training like a checkbox.

Onboard fast.

Move faster.

Fill in gaps later.

Repeat.

But every time you push off training, you create debt.

Training debt.

It doesn’t show up immediately, which is why it’s so easy to ignore. At first, things seem fine. Then people hesitate. Deliverables wobble. Standards get fuzzy. And the inevitable drag begins.

Since selling Pneuma, I’ve been doing more consulting (returning to my roots). As parts of my engagements, I do a Waypoint with nearly every person on a client’s team (more on that in a past issue. You can find a guide to Waypoints in the resource doc at the bottom or linked above).

One theme cuts across every business I’ve worked with, can you guess what it is?

Drumroll please 🥁 

People want, and need, direction.

Not because they’re new. Not because they’re incapable. Because the standards, structure, and expectations haven’t been made permanent.

You hear it in subtle ways.

“I wish I knew exactly what they wanted.”

“I’m not sure if I can run with this or if I need to check first.”

“Why does this keep coming back with revisions?”

“I think I need to do this next, what are your thoughts?”

When people don’t understand the bar - or when the bar keeps moving - you create a kind of operational fragility. Managers step in to rework what should have been fully delegated. Work gets stuck in limbo while teams wait for a green light. Feedback turns emotional because neither side is working from shared definitions of quality. These aren’t execution problems. They’re clarity problems. And clarity, more often than not, is a direct function of training.

The trouble is, most people treat training as a one-time event or a pile of documents to revisit later. Something you do during week one or hand off to HR. Telling people how to use Slack and Google Calendar. But real training is ongoing, and it’s certainly not just functional guides on how to use tools. It teaches people not only how to do something, but how we think about doing it.

That includes:

• What quality looks like when no one’s looking

• How decisions should get made under pressure

• When to act and when to escalate

• What “ownership” actually means in practice

When this guidance is missing - or worse, inconsistent - you force your team to guess.

And from experience, guessing doesn’t scale.

It does move fast, which make it feel like scale, but it’s not true scale.

And the real problem isn’t speed anyways. It’s skipping the foundational work of making how you operate clear, repeatable, and durable. Because every time you rely on “they’ll figure it out,” you’re rolling a dice you didn’t need to roll. One missed expectation becomes two. Two turns into four. Soon you’re spending half your week “fixing” things that should have been clean from the start.

This is how training debt compounds. Slowly, then suddenly.

It’s easy to trace the origin back to some internal deadline or a quarterly rock you decided was urgent. Something you said you had to hit by Q2, or a launch you had to push by Friday. But unless you're building in a true zero-sum, winner-take-all market (spoiler: you're probably not), that urgency is self-imposed. The goal was arbitrary. The rush was optional.

And in trying to move faster, you moved sloppier.

And as you moved sloppier, you decreased the probability of “winning” to begin with.

In trying to build quickly, you built brittle instead.

And who wants a brittle business?

Now, enough with recognizing the problem - let’s talk about something I put in place at Pneuma that helped build an organization that both “got the bigger picture”, and knew what to do in the small, detailed, tactical moments.

Working Theories

Building some level of clarity, at scale, is not easy.

And to be frank, it was one of the more challenging things running Pneuma. It required me to continually harp on the same 2-3 things, over and over and over, to build a permanent understanding of our business, why we existed, and what we did better than others.

That’s when the Friday Note, later named the “Beacon”, was introduced.

It’s one of the simplest things you can do as an owner/founder, that will have the largest impact on the business.

More on the Friday Note below.

Resources

Doc Referenced In The Video

Full List Of Working Theories