Issue #26 & July 6th, 2026
Happy Monday!
In January I wrote about designing a firm that scales in 2026. I thought SOPs were the answer: document everything, hand off the work.
It turns out I was missing an entire layer. That's what this issue is about.
Before we get into it - I'm speaking at Bridging the Gap in Charlotte July 28–30, and at Intuit Connect later this fall.
If you'll be at either, hit reply. I'd love to meet up!
The Judgment Layer
Have you ever built a beautiful Loom video or step by step direction but still get the questions like “I followed the steps but there’s a $200 discrepancy” or “This month something on the payroll entry is different, what do I do?”
At Celerity, we’ve been building playbooks for all that we do. Client by client, by accounting system, and even about how we communicate with clients.
We did everything the delegation gurus said. Documented everything. Beautiful playbooks. The questions kept coming.
Not because the team didn’t know the steps. But because they didn’t know how to think when something didn’t match those steps.
You can’t really checklist or document judgment and discernment. That takes a different kind of coaching.
The Realization
Accounting isn’t just a series of tasks. If it were, AI would already have taken our jobs.
It’s actually a series of decisions to make.
Should we ask the client about this?
Should this be accrued?
Does this seem unusual?
Is this material for this client?
Can this wait until next month?
Do we just fix it or educate the client?
These aren’t process questions.
They’re judgment questions.
The “judgment layer”
Every single role at a firm has two layers.
Layer 1 is the execution. Following the checklist, completing the reconciliations, closing the month. That's what SOPs typically can cover.
Layer 2 is different:
Knowing when the checklist no longer applies.
Recognizing patterns and things worth reaching out about.
Understanding the tradeoffs.
Making decisions without complete information.
This is the judgment layer.
And that's where people become seniors, controllers, and advisors at a firm.
Where leaders get stuck
This is where delegation can get stuck for leaders.
Someone asks:
“What do I do in this situation?”
You answer and give them exactly what to do because it’s faster.
And they ask again, and again.
Eventually you realize that you’ve created a dependency instead of fully delegating something.
What I’ve started to do to fix this
Instead of immediately answering or solving their issue, we try asking:
What would you do?
or
Walk me through your thinking
or
What have you tried or considered so far?
And when their reasoning is correct, we don’t just move on. We write it down.
That answer becomes a decision rule in the playbook. “If the difference is under $x, and it’s a timing issue, just book it; If it’s unexplained, flag it and ask the client” This question trains the person and the written rule trains the firm.
With questions like these, you’re no longer just solving today’s problem.
You’re training them on tomorrow’s judgment so they don’t need to come to you so often.
Procedures create consistency.
Judgment creates scale.
The firms that grow fastest aren’t those with the best process manuals.
They’re the firms that equip their team with the tools to make their own judgment calls and decisions.
Processes tell people what to do exactly.
Judgment tells people what to do when the process runs out.
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Steal this The Takeaways • Stop just answering the question - ask "walk me through your thinking" first. • When their reasoning is right, have them document it. Answers become decision rules in the playbook. • SOPs create consistency. Judgment creates scale. "Every question that reaches you is a decision rule waiting to be written." |
Question of the week
How many decisions in your firm exist only in your head?
Here’s to answering fewer questions!
Have a lovely week,
- Tailor
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