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Productivity prompt

Growing From Founder to 34 People Without Losing the Team You Built

Every winery that outgrows the founder-does-everything stage hits the same wall: the practices that kept five people loyal do not automatically scale to thirty. Here is how to decide which of your informal perks become written policy before your next hiring push.

How to use it

  1. Copy the prompt below.
  2. Swap each [bracket] for your own details. The more specific you are, the better the answer.
  3. Paste it into Claude, ChatGPT, or Gemini and send it.

The prompt

You are an HR operations advisor who works with small wine, beer, and spirits businesses. I run [WINERY/BREWERY/DISTILLERY/DISTRIBUTOR NAME] in [STATE/REGION]. We have [NUMBER] employees across [DEPARTMENTS, e.g., tasting room, cellar, DTC/club, sales, admin], and we are planning to hire [NUMBER] more in the next [TIMEFRAME].

Here are the informal practices and promises we currently run on, written exactly as they happen in real life:
[PASTE YOUR LIST, e.g., "tasting room staff can swap shifts by text with each other," "harvest crew gets comp bottles after crush," "club manager works from home Fridays," "I approve time off verbally, no form"]

Do three things:

1. Sort each practice into KEEP INFORMAL, WRITE DOWN NOW, or FIX BEFORE WRITING DOWN. For each one, give me one sentence on why, written for an owner, not an HR department.

2. For everything in WRITE DOWN NOW, draft the policy language in plain English, under 100 words each. No corporate filler. It should sound like a person wrote it.

3. Flag every practice that could create a wage-and-hour, classification, tip-pooling, or overtime question in my state, and tell me the specific question to ask an employment attorney about it. Do not give me legal conclusions, give me the question.

Then push back on me: name the two practices on my list that are most likely to cause a fairness complaint once we grow past [NUMBER] people, and tell me what I am avoiding dealing with. Be direct.

What you fill in

  • WINERY/BREWERY/DISTILLERY/DISTRIBUTOR NAME
  • STATE/REGION
  • NUMBER
  • DEPARTMENTS, e.g., tasting room, cellar, DTC/club, sales, admin
  • TIMEFRAME

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