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Last time, we took a task we’d solved before and turned it into a playbook.

We captured the steps, listed what was needed, defined what “done” looked like, and tested the instructions on a fresh example.

The point was simple: the next time the problem appeared, we shouldn’t have to start from scratch.

But writing the playbook is only part of the job.

Imagine you save it in a folder. A month passes and someone on the team runs into the same problem.

They don’t know the playbook exists so they solve it their own way.

Or they find the document, follow the steps, and discover that one of the instructions no longer applies.

The work was documented. The problem still came back.

HERE’S WHAT WE LEARNED.

It’s easy to treat documentation as the finish line.

You solved the problem.

You wrote down the process.

You saved the file.

Done.

But a useful playbook has to survive three things:

Don’t make someone remember a separate folder, search through old messages, or ask who documented the process.

Put the link where the task is already managed: the project page, team workspace, task template, or checklist people use when the problem comes up.

The best place depends on how your team works. 

The principle is simple: 

Make the next step to the playbook obvious at the moment someone needs it.

The owner doesn’t have to do all the work. They’re responsible for checking whether the playbook still matches reality and arranging an update when it doesn’t.

You don’t need to review every playbook every week. Choose a review date that makes sense for how often the process changes and how much it matters if the instructions become outdated.

USE AI TO FIND WHAT NEEDS CHECKING

🔴🟡🟢 COPY THIS INTO CHATGPT OR YOUR AI TOOL:

Act as my process review assistant.

Review the playbook below against the current process information I provide.

Identify:

  • Steps that may no longer match the current process

  • Outdated tools, roles, links, or requirements

  • Missing steps or unclear instructions

  • Any difference between the playbook and the current information

  • Questions the owner needs to resolve before updating it

For each item, distinguish what the source explicitly says from what may need clarification.

Rules:

  • Do not assume a step is outdated without evidence.

  • Do not invent replacements for missing information.

  • Separate confirmed differences from items that need checking.

  • If the information is insufficient, say what needs to be verified.

  • Mark anything that needs checking as [NEEDS CONFIRMATION]

Playbook:

[Paste the current playbook.]

Current process information:

[Paste the latest confirmed steps, requirements, or changes.]

Owner:

[Name or role]

Last reviewed:

[Date]

Proposed review date:

[Date]

Review the output against the actual process.

AI can help you spot differences. It cannot independently confirm that your team has changed a process or that a new instruction is correct.

The owner still needs to verify the changes and update the playbook.

The improvement isn’t more documentation.

It’s making the documentation usable.

Season 2 wraps up soon.

You made the brief clearer.

You caught the warning earlier.

You wrote the handoff and the playbook.

Then someone else picks it up.

They read the note and ask the one question you didn't think of. They follow the playbook their own way. They review the work and say "looks good."

Same work. More people. A whole new set of problems.

Season 3 starts next Tuesday. Titled: Working Together.

You can get ahead on your own work. What happens when the work involves other people?