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You made the rule. The system never got the memo.

Six months ago you changed your pricing. Told the team in the strategy session. Wrote it in the notes. And last quarter you found out your reps were still sending the old number.

Not because they ignored you. Because the template never changed.

That's not a people problem. That's where rules go to die.

Here's the root cause: documenting a rule and implementing a rule are two different acts. Most teams do the first and call it done. The second — opening the tool, updating the template, changing the sequence — gets skipped. Every time.

The fix is unglamorous: rule-writing and rule-updating have to be one act. The moment the decision is made, the system gets updated. Not at the next team meeting. Now, while the room is still together.

Sound familiar?

"We only call qualified leads." Lives in a Notion doc. The CRM sequences haven't changed.

"Follow up within 24 hours." Decided in a sales meeting. The workflow still waits three days.

"We price at X, not Y." Set in a strategy session. The proposals still go out with Y.

"Discovery call must ask these five questions." In the onboarding doc. The reps have never read it.

Every founder I know has a dozen of these. Documented rules that haven't touched the actual system. They feel like implementation. They are not.

Here's the test that makes this real.

If your best salesperson quit tonight, would the rule survive tomorrow?

If the answer depends on someone remembering to brief the replacement.. it's not a rule yet. It's an intention. A rule becomes real the moment it lives in the tool, the template, the checklist, or the sequence that runs without you.

The Lotto Test: if you won the lottery on Friday and stopped showing up Monday, which of your rules would still run? Those are your real rules. Everything else is a wish.

Three moves to close the gap.

1. Ask: where does the work actually happen?

That's where the rule must live. In the CRM. In the email template. In the call script. Before you close the meeting, open the tool and make the change. Schedule thirty minutes the same day if you can't do it in the room. After 24 hours, it won't happen.

2. Do a monthly rules sweep.

Once a month, thirty minutes: what did we decide last month, and is it in the tool? Two options for every item on the list — wire it in, or delete it. A rule you're not willing to update the system for isn't a rule. It's a preference. Preferences don't run pipelines.

3. Run the Lotto Test on your sales process.

Write down the five rules your pipeline depends on. For each one: does it run automatically, or does it run because someone remembers? Every "someone remembers" is a gap. Work through the list, one rule per week.

Your sales cycle lives or dies in the gap between what you decided and what actually runs. The 24-hour follow-up that takes three days costs you deals. The proposals at the wrong price cost you margin. The unqualified leads cost your team focus.

Every one of those is a rule that didn't make it into the system.

Pick the one that's costing you most. Find where the work happens. Wire it in before this week ends.

I put together a one-page question set I use with clients to find these gaps in under thirty minutes — the five questions that surface the rules most likely to be broken. If you want it, reply with "rules audit" and I'll send it directly.

Keep rolling.. Simon

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A collection of gems.

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